Chloroacetic Acid → 2-Cyclohexylideneacetic acid

HRID 1660311

반응식

HRID 1660311 반응식
P([O-])(OCC)OCC.[H-].[Na+].Cl[CH2:12][C:13]([OH:15])=[O:14].[H][H].[C:18]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>COCCOC>[C:18]1(=[CH:12][C:13]([OH:15])=[O:14])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

참가 물질

7

반응물 5

HCID 300Chloroacetic AcidHCID 7967CyclohexanoneHCID 24758Sodium hydrideHCID 3780918DiethylphosphiteHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 962062-Cyclohexylideneacetic acid수율 54.1%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

실험 절차

A mixture of 4.0 ml (0.031 mole) of diethyl phosphite and 4.46 g (0.093 mole) of 50% sodium hydride in mineral oil in 100 ml of 1,2-dimethoxyethane under nitrogen was treated with a solution of 2.93 g (0.031 mole) of chloroacetic acid in 30 ml of 1,2-dimethoxyethane, and the mixture was stirred until hydrogen gas evolution ceased. Then 3.20 ml (0.031 mole) of cyclohexanone was added and the mixture was stirred for 1 h, after which it was quenched by the addition of 5 ml of ethanol and then poured into 500 ml of water. The strongly basic solution was washed with ether to remove mineral oil (ether extract discarded), then acidified to pH 4 with conc hydrochloric acid and extracted with ether. The ether extract was dried (over MgSO4) and evaporated in vacuo to yield 2.35 g (54%) of cyclohexylideneacetic acid which was recrystallized from methanol/water; mp 90°-91.5° (literature mp 90°-92°, Beesley, Thorpe, and Ingold, J. Chem. Soc., 107, 1099 (1915)); Ir (CHCl3) 3600-2400 (--OH), 1700 (C=O), and 1650 (C=C) cm-1 ; 1H NMR (CDCl3) δ 1.60 (6, s, CH2CH2CH2CH 2 CH2C=), ##STR8## 5.50 (1, s, =CHCO2H), and 11.40 (1, s, --CO2H); Anal Calcd for C8H12O2 : C, 68.55; H, 8.63; Found: C, 68.45; H, 8.61.

후처리

  1. customafter which it was quenched by the addition of 5 ml of ethanol
  2. additionpoured into 500 ml of water
  3. washThe strongly basic solution was washed with ether
  4. customto remove
  5. extractionmineral oil (ether extract discarded)
  6. extractionextracted with ether
  7. extractionThe ether extract
  8. dry with materialwas dried (over MgSO4)
  9. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-ac5aafcc020a40d0a95eaca95dd4b245
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04307232

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