Dimethylformamide → p-Acetoxybenzoyl chloride

HRID 630305Notes

Reaction equation

HRID 630305 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 2756254p-Acetoxybenzoyl chlorideYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-5fdcfd3f18854b118dcb02f33ef4b929
Source dataset
uspto-grants-2016_04
Patent number
US09315509B2

Reaction notes

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