\u00a0<\/strong><\/p>\n<\/td>\n

wt\/vol<\/p>\n<\/td>\n

MW<\/p>\n<\/td>\n

moles<\/p>\n<\/td>\n

density<\/p>\n<\/td>\n

equivs.<\/p>\n<\/td>\n

yield<\/p>\n<\/td>\n<\/tr>\n

I<\/strong><\/p>\n<\/td>\n

17.966 g<\/p>\n<\/td>\n

442.65<\/p>\n<\/td>\n

0.0406<\/p>\n<\/td>\n

\n<\/td>\n

1.0<\/p>\n<\/td>\n

\n<\/td>\n<\/tr>\n

II<\/strong><\/p>\n<\/td>\n

19.10 mL<\/p>\n<\/td>\n

102.09<\/p>\n<\/td>\n

0.2024<\/p>\n<\/td>\n

1.082<\/p>\n<\/td>\n

5.0<\/p>\n<\/td>\n

\n<\/td>\n<\/tr>\n

III<\/strong><\/p>\n<\/td>\n

22.60 mL<\/p>\n<\/td>\n

101.19<\/p>\n<\/td>\n

0.1621<\/p>\n<\/td>\n

0.726<\/p>\n<\/td>\n

4.0<\/p>\n<\/td>\n

\n<\/td>\n<\/tr>\n

IV<\/strong><\/p>\n<\/td>\n

0.496 g<\/p>\n<\/td>\n

122.17<\/p>\n<\/td>\n

0.0041<\/p>\n<\/td>\n

\n<\/td>\n

0.1<\/p>\n<\/td>\n

\n<\/td>\n<\/tr>\n

V<\/strong><\/p>\n<\/td>\n

400 mL<\/p>\n<\/td>\n

–<\/p>\n<\/td>\n

–<\/p>\n<\/td>\n

\n<\/td>\n

\n<\/td>\n

\n<\/td>\n<\/tr>\n

VI<\/strong><\/p>\n<\/td>\n

18.440 g<\/p>\n<\/td>\n

484.69<\/p>\n<\/td>\n

0.0380<\/p>\n<\/td>\n

\n<\/td>\n

\n<\/td>\n

(94%)<\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<\/div>\n

 <\/p>\n

Procedure:<\/strong>\u00a0\u00a01000 mL 1-neck flask, stirbar, septum, N_{2<\/sub>\u00a0inlet<\/p>\n}

Dissolved 17.966 g of alcohol\u00a0I<\/strong>\u00a0in 400 mL of dry CH_{2<\/sub>Cl2<\/sub>.\u00a0\u00a0Stirred at rt.\u00a0Added 19.10 mL of Ac2<\/sub>O followed by 22.6 mL of Et3<\/sub>N and 0.469 g of DMAP.\u00a0After 3h, quenched with sat. aq. NH4<\/sub>Cl.\u00a0\u00a0Extracted with CH2<\/sub>Cl2<\/sub>.\u00a0\u00a0The organic layer was dried over MgSO4<\/sub>, filtered and the solvent was removed by rotary evaporation.\u00a0The product was isolated by flash chromatography on silica gel using 10:90 EtOAc-hexanes as eluant.\u00a0\u00a0The product was a clear, colorless oil.<\/p>\n}

 <\/p>\n

[a]_{D<\/sub>\u00a0+11.00 (c = 1.82, CH2<\/sub>Cl2<\/sub>).<\/p>\n","protected":false},"excerpt":{"rendered":"}

MECHANISM   In\u00a0\u00a0this reaction an acyl pyridium ion is formed which is the reactive species.\u00a0\u00a0Facile addition of the alcohol to the acyl pyridinium ion regenerates DMAP and, after loss of the oxonium proton to acetate, forms the desired product plus acetic acid which is scavenged by Et3N. reaction— \u00a0 wt\/vol MW moles density equivs. yield… Continue reading ACETYLATION MECHANISM<\/span><\/a><\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[3],"tags":[143],"_links":{"self":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/48"}],"collection":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/comments?post=48"}],"version-history":[{"count":1,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/48\/revisions"}],"predecessor-version":[{"id":49,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/48\/revisions\/49"}],"wp:attachment":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/media?parent=48"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/categories?post=48"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/tags?post=48"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}