Dimethylformamide → p-Acetoxybenzoyl chloride

HRID 16471

반응식

HRID 16471 반응식
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].CN(C=O)C.C(Cl)(=O)C([Cl:22])=O>C(Cl)Cl>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:22])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 16865Benzoic acid, 4-(acetyloxy)-HCID 65578Oxalyl chloride

생성물 1

HCID 2756254p-Acetoxybenzoyl chloride수율 99.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A slurry of 4-acetoxybenzoic acid (100 g, 555.1 mmol) in CH2Cl2 (50 mL) was treated with a catalytic amount of DMF (0.5 mL) and cooled in ice bath. The reaction was stirred as neat oxalyl chloride (51 mL, 582.82 mmol, 1.05 equiv.) was added dropwise. The reaction was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure to give 4-(chlorocarbonyl)phenyl acetate (110 g, 100% th.; 110% pract.), which was used in the next step without further purification; 1H NMR (CDCl3) δ 8.09 (d, 2H), 7.20 (d, 2H), 2.28 (s, 3H) ppm.

후처리

  1. temperaturecooled in ice bath
  2. additionwas added dropwise
  3. concentrationThe reaction mixture was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d168becfdd444e75bda3c5483bb48d6d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737145B2

연결된 노트

불러오는 중…