Dimethylformamide → p-Acetoxybenzoyl chloride

HRID 1741823Notes

Reaction equation

HRID 1741823 reaction equation
CN(C)C=O.[C:6]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1)(=[O:8])[CH3:7].C(Cl)(=O)C([Cl:22])=O>ClCCl>[C:6]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([Cl:22])=[O:15])=[CH:12][CH:11]=1)(=[O:8])[CH3:7]

Participants

5

Reactant 3

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

Product 1

HCID 2756254p-Acetoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Dimethylformamide (0.5 ml) was added to a solution of 4-acetoxybenzoic acid (50 g) and oxalyl chloride (27 ml) in dichloromethane (500 ml). The mixture was stirred for 2 hours at room temperature. The solvent was evaporated and the residue was dissolved in n-hexane (200 ml). After filtration, the solution was evaporated to give 4-acetoxybenzoyl chloride as a yellow oil (55.1 g).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in n-hexane (200 ml)
  3. filtrationAfter filtration
  4. customthe solution was evaporated

Sources & evidence

ORD record
ord-2e61c963a42f432a9bc6c2ee448f3625
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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