Sodium Hydroxide → 8-Acetyl-12-hydroxyheptadec-10-ynoic acid

HRID 1833776노트

반응식

HRID 1833776 반응식
[C:1]([C:4]([CH2:21][C:22]#[C:23][CH:24]([O:30]C(=O)C)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])C(OCC)=O)(=[O:3])[CH3:2].[OH-].[Na+]>O.CO>[C:1]([CH:4]([CH2:21][C:22]#[C:23][CH:24]([OH:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 20322248Diethyl 2-acetyl-2-(4-acetoxy-2-nonyn-1-yl)azelate

생성물 1

HCID 203222518-Acetyl-12-hydroxyheptadec-10-ynoic acid수율 36.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of diethyl 2-acetyl-2-(4-acetoxy-2-nonyn-1-yl)azelate (59.7 g., 0.128 mole) and sodium hydroxide (30 g., 0.75 mole) in water (200 ml.) and methanol (800 ml.) is heated at 60° for 16 hours. Most of the methanol is then distilled at reduced pressure and the residue is dissolved in water. The solution is acidified to Congo Red with hydrochloric acid and the oily product taken up in ether and dried over sodium sulfate. Evaporation of the ether leaves 41.1 g. of the crude product as a reddish viscous oil. The product is purified by chromatography on 650 g. of silica gel with 2% methanol in chloroform as eluant. Fifteen grams of pure 8-acetyl-12-hydroxy-10-heptadecynoic acid is obtained as a yellow viscous oil; pmr (CDCl3) δ0.90 (3H,t), 2.20 (3H,s CH3CO), 4.37 (1H,t HCO).

후처리

  1. distillationMost of the methanol is then distilled at reduced pressure
  2. dissolutionthe residue is dissolved in water
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of the ether
  5. customleaves 41.1 g
  6. customThe product is purified by chromatography on 650 g

출처 및 근거

ORD 기록
ord-7cac23ca41d34b91b0551018f0586863
출처 데이터셋
uspto-grants-1978_01
특허 번호
US04066692

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