Dimethylformamide → p-Acetoxybenzoyl chloride

HRID 16471

反応式

HRID 16471 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 2756254p-Acetoxybenzoyl chloride収率 99.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-d168becfdd444e75bda3c5483bb48d6d
出典データセット
uspto-grants-2010_06
特許番号
US07737145B2

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