{"id":8901,"date":"2015-04-28T15:48:52","date_gmt":"2015-04-28T20:48:52","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=8901"},"modified":"2025-09-24T10:09:42","modified_gmt":"2025-09-24T15:09:42","slug":"elimination-of-alcohols-to-alkenes-with-pocl3","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2015\/04\/28\/elimination-of-alcohols-to-alkenes-with-pocl3\/","title":{"rendered":"Elimination of Alcohols To Alkenes With POCl3"},"content":{"rendered":"<p><strong>POCl<sub>3<\/sub> For The Elimination Of Alcohols To Alkenes<\/strong><\/p>\n<p>Phosphorus oxychloride (POCl<sub>3<\/sub>) is a useful reagent for cleanly performing elimination reactions on alcohols.<\/p>\n<ul>\n<li>POCl<sub>3<\/sub> converts the OH group into a good leaving group<\/li>\n<li>A base such as pyridine is generally added, which performs an E2 elimination to give the more substituted double bond<\/li>\n<li>Elimination occurs without rearrangements.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-15221\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-phosphorus-oxychloride-pocl3-is-a-dehydration-reagent-for-alcohols-leads-to-formation-of-alkenes-when-pyridine-is-added-.gif\" alt=\"phosphorus oxychloride pocl3 is a dehydration reagent for alcohols leads to formation of alkenes when pyridine is added\" width=\"600\" height=\"307\" \/><\/p>\n<p>Table Of Contents<\/p>\n<ol>\n<li><a href=\"#one\">Two Ways To Convert Alcohols\u00a0 To Alkenes We&#8217;ve Learned Previously<\/a><\/li>\n<li><a href=\"#two\">Direct Elimination of Alcohols To Alkenes With POCl<sub>3<\/sub>:\u00a0 The Mechanism<\/a><\/li>\n<li><a href=\"#three\">The Reaction Works For Primary, Secondary, and Tertiary Alcohols<\/a><\/li>\n<li><a href=\"#four\">Summary: Direct Elimination of Alcohols With POCl<sub>3<\/sub><\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. Two\u00a0 Ways To Convert Alcohols To Alkenes We&#8217;ve Learned Previously<\/strong><\/h2>\n<p>Here&#8217;s what we talk about today: more eliminations of alcohols! \u00a0Note that this reagent isn&#8217;t covered in all courses, but I&#8217;ll\u00a0include it here for completeness&#8217; sake.<\/p>\n<p>We&#8217;ve talked about 2 ways to convert alcohols to alkenes so far:<\/p>\n<ul>\n<li><strong>Option #1:\u00a0<\/strong>Convert the alcohol to an alkyl halide [with SOCl<sub>2<\/sub>, PBr<sub>3<\/sub>, or a hydrohalic acid] and then treat with a strong base like NaOEt or similar to produce the alkene through an E2 process\u00a0 [2 operations]<\/li>\n<li><strong>Option #2:<\/strong>\u00a0Heat the alcohol with a strong non-nucleophilic acid like H<sub>2<\/sub>SO<sub>4<\/sub> or H<sub>3<\/sub>PO<sub>4<\/sub> [1 operation]. [<a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/04\/16\/elimination-reactions-of-alcohols\/\" target=\"_blank\" rel=\"noopener noreferrer\">see post<\/a>]<\/li>\n<\/ul>\n<p>So which is better? Well, actually they both have their drawbacks.<\/p>\n<ul>\n<li>\u00a0Converting an alcohol to an alkyl halide followed by treatment with base is two separate operations. This is OK, but it would be nice to be able to do this in one step.<\/li>\n<li>Heating alcohols with strong acids is a one-step process, but can lead to <strong>carbocation rearrangements.<\/strong> Ideally we&#8217;d like to have better control of the products of these reactions, and avoid byproducts that come from hydride or alkyl shifts.<\/li>\n<\/ul>\n<p>Before we go any further, you might think this is nitpicky. You might think, &#8220;two steps! Who cares!! What&#8217;s the big deal?&#8221; .<\/p>\n<p>The big deal is &#8211; we CARE about our time &#8211; a lot!<\/p>\n<p>Think about how much you hate it when a website takes more than 3 seconds to load. People will walk through a nicely manicured garden to shave five\u00a0seconds off their journey.<\/p>\n<p>Chemists are no different. If there&#8217;s a way to do something in one step instead of two, we&#8217;ll take it! So yes, one step instead of two matters to us.<\/p>\n<p>Today we talk about a process that gives us the best of both worlds &#8211; a one-step process that proceeds under much milder conditions than heating with acid.<\/p>\n<p>It doesn&#8217;t get covered in all introductory organic chemistry courses, but for completeness, we&#8217;ll cover it here.<\/p>\n<h2><a id=\"two\"><\/a>2. Direct Elimination of Alcohols To Alkenes With Phosphorus Oxychloride (POCl<sub>3<\/sub>)<\/h2>\n<p>Hydroxide (HO- ) is a very poor leaving group. In order for alcohols to participate in substitution and elimination reactions, it&#8217;s best to modify the oxygen in some way so as to be able to stabilize the negative charge generated when the C-O bond breaks.<\/p>\n<p>One way we&#8217;ve seen how to do this is by converting alcohols to <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/03\/10\/tosylates-and-mesylates\/\" target=\"_blank\" rel=\"noopener noreferrer\">alkyl sulfonates, such as tosylates or mesylates<\/a>.<\/p>\n<p>It would also work if we converted an alcohol to an alkyl phosphate [itself a good leaving group], but as it turns out the OH groups on phosphate are acidic and can interfere with the basic reagents we typically use for elimination. So a compromise is to use the reagent <strong>phosphorus oxychloride<\/strong> (POCl<sub>3<\/sub>), a derivative of phosphoric acid. \u00a0When POCl<sub>3<\/sub> is added to an alcohol, we form a new O-P bond [the oxygen phosphorus bond is strong] and break a P-Cl bond to form what we could call a &#8220;chlorophosphate ester&#8221;.<\/p>\n<p>This is now a good leaving group! If we have a decent base around [such as pyridine] we can then get elimination of this good leaving group to form a new alkene [via E2].<\/p>\n<p>In practice an excess of pyridine is used here, or even use pyridine as the solvent.<\/p>\n<p>Here&#8217;s how it works:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-26295\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2022\/08\/1-mechanism-for-reaction-of-alcohols-with-pocl3-in-the-presence-of-pyridine-to-give-alkene-generally-gives-zaitsev-product-1.gif\" alt=\"mechanism for reaction of alcohols with pocl3 in the presence of pyridine to give alkene generally gives zaitsev product-1\" width=\"640\" height=\"500\" \/><\/a><\/p>\n<p>This process proceeds in on operation, is much milder than heating an alcohol with strong acid and doesn&#8217;t result in rearrangements.<\/p>\n<h2><a id=\"three\"><\/a>3. The Reaction Works For Primary,\u00a0 Secondary, and Tertiary Alcohols<\/h2>\n<p>It works for primary, secondary, and tertiary alcohols.<br \/>\n<img decoding=\"async\" class=\"alignnone wp-image-15224\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-pocl3-to-give-elimination-reactions-of-alcohols-examples-of-alkenes-that-are-formed-zaitsev-rule-applies-trans-alkenes-favored-over-cis-alkenes-1.gif\" alt=\"pocl3 to give elimination reactions of alcohols examples of alkenes that are formed zaitsev rule applies trans alkenes favored over cis alkenes\" width=\"600\" height=\"478\" \/><\/p>\n<p>Like I said it doesn&#8217;t appear in all introductory courses but it&#8217;s important to know that when you see it, think &#8220;elimination&#8221;. <strong>Importantly, don&#8217;t confuse this reagent with PBr<sub>3<\/sub> or PCl<sub>3<\/sub><\/strong> &#8211;&gt; those will convert an alcohol to an alkyl halide, which is not the same reaction at all!<\/p>\n<h2><a id=\"four\"><\/a>4. Summary:\u00a0 Direct Elimination\u00a0 of\u00a0 Alcohols To Alkenes With <strong>POCl<sub>3<\/sub><\/strong><\/h2>\n<p>This is all we&#8217;ll have to say about substitution and elimination reactions of alcohols, for now. In the next few posts, we&#8217;ll go through a special property of alcohols &#8211; the ability of certain reagents to lead to their &#8220;oxidation&#8221; to species such as aldehydes, ketones, and carboxylic acids. More next time!<\/p>\n<p><strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/05\/06\/alcohol-oxidation-strong-and-weak-oxidants\/\">Alcohol Oxidation &#8211; &#8220;Strong&#8221; and &#8220;Weak&#8221; Oxidants<\/a><\/strong><\/p>\n<hr \/>\n<h2><a id=\"notes\"><\/a>Notes<\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/05\/06\/alcohol-oxidation-strong-and-weak-oxidants\/\" class=\"\"><span>Alcohol Oxidation: \u201cStrong\u201d and \u201cWeak\u201d Oxidants<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/04\/16\/elimination-reactions-of-alcohols\/\" class=\"\"><span>Elimination Reactions of Alcohols<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2020\/04\/30\/alkene-stability\/\" class=\"\"><span>Alkene Stability<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/09\/27\/the-e2-mechanism\/\" class=\"\"><span>The E2 Mechanism<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/03\/10\/tosylates-and-mesylates\/\" class=\"\"><span>Tosylates And Mesylates<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/03\/20\/pbr3-and-socl2\/\" class=\"\"><span>PBr3 and SOCl2<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/09\/10\/elimination-reactions-are-favored-by-heat\/\" class=\"\"><span>Elimination Reactions Are Favored By Heat<\/span><\/a><\/li><\/ul><\/div>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/h2>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3414-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3415-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3416-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3417-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3418-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n<hr \/>\n<p><strong><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/strong><\/p>\n<ol>\n<li><strong>The Effect of Structure on the Course of Phosphoryl Chloride-Pyridine Dehydration of Tertiary Alcohols<br \/>\n<\/strong>Ronald R. Sauers<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society <\/em><strong>1959 <\/strong><em>81<\/em>(18), 4873-4876<strong><br \/>\nDOI:\u00a0<\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja01527a028\">10.1021\/ja01527a028<\/a><\/li>\n<li><strong>Stereospecificity and regiospecificity of the phosphorus oxychloride dehydration of sterol side chain alcohols<br \/>\n<\/strong>Jose Luis Giner, Christian Margot, and Carl Djerassi<br \/>\nThe Journal of Organic Chemistry <strong>1989 <\/strong><em>54<\/em>(2), 369-373<strong><br \/>\nDOI:\u00a0<\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo00263a020\">10.1021\/jo00263a020<\/a><br \/>\nThis article by the legendary chemist Carl Djerassi (who developed norethindrone, the first female contraceptive) describes the selectivity of POCl<sub>3<\/sub>-pyridine dehydration conditions in steroid synthesis. It also has a general procedure for POCl<sub>3<\/sub>-pyridine dehydration in the experimental section.<\/li>\n<li><strong>A general approach to linearly fused triquinane natural products. Total syntheses of (.+-.)-hirsutene, (.+-.)-coriolin, and (.+-.)-capnellene<br \/>\n<\/strong>Goverdhan Mehta, A. Narayana. Murthy, D. Sivakumar. Reddy, and A. Veera. Reddy<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society <\/em><strong>1986<\/strong><em>108<\/em>(12), 3443-3452<strong><br \/>\nDOI:\u00a0<\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ja00272a046\">10.1021\/ja00272a046<\/a><br \/>\nThis paper by Prof. Goverdhan Mehta demonstrates the applicability of the POCl-pyridine dehydration in natural product total synthesis.<\/li>\n<li><strong> The 3-methylcholestanols and their derivatives<br \/>\n<\/strong>D. H. R. Barton, A. da S. Campos-Neves\u00a0 and\u00a0 R. C. Cookson<br \/>\n<em>J. Chem. Soc., <\/em><strong>1956<\/strong><em>, <\/em>3500-3506<br \/>\n<strong>DOI:\u00a0<\/strong><a href=\"https:\/\/pubs.rsc.org\/en\/Content\/ArticleLanding\/JR\/1956\/JR9560003500#!divAbstract\">10.1039\/JR9560003500<\/a><br \/>\nThis paper by Nobel Laureate Prof. Derek H. R. Barton has a POCl<sub>3<\/sub>-pyridine dehydration (see p. 3504-3505 in the experimental section).<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>POCl3 For The Elimination Of Alcohols To Alkenes Phosphorus oxychloride (POCl3) is a useful reagent for cleanly performing elimination reactions on alcohols. POCl3 converts the <\/p>\n","protected":false},"author":1,"featured_media":15221,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1420],"tags":[169,1034,473,201,1062],"post_folder":[],"class_list":["post-8901","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alcohols-epoxides-ethers","tag-alkenes","tag-dehydration","tag-e2","tag-elimination","tag-pocl3"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Elimination of Alcohols To Alkenes With POCl3 and Pyridine<\/title>\n<meta name=\"description\" content=\"POCl3 with pyridine is a handy combination of reagents to perform the direct elimination of alcohols to alkenes. 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