Dimethylformamide → Benzeneacetyl chloride, 4-(acetyloxy)-

HRID 1463440Notes

Reaction equation

HRID 1463440 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].CN(C)C=O.C(Cl)(=O)C([Cl:23])=O>C(Cl)Cl>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([Cl:23])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2415872-(4-(Acetyloxy)phenyl)acetic acid

Product 1

HCID 182488Benzeneacetyl chloride, 4-(acetyloxy)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

250 mg of p-acetoxyphenylacetic acid was dissolved in 5 ml of methylene chloride. To the solution were added, with ice cooling, a catalytic amount of N,N-dimethylformamide and 0.12 ml of oxalyl chloride. The mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure to obtain p-acetoxyphenylacetyl chloride. This compound was dissolved in 5 ml of methylene chloride. To the solution was added 260 mg of a sulfur trioxide-dioxane complex with ice cooling. The mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure to obtain DL-2-(p-acetoxyphenyl)-2-sulfoacetyl chloride. This compound was dissolved in 5 ml of anhydrous tetrahydrofuran.

Workup

  1. additionTo the solution were added, with ice cooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8e62da2d1f314fc2909d81dbd7f1711c
Source dataset
uspto-grants-1994_04
Patent number
US05300497

Reaction notes

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