(4-Nitrophenyl)acetic acid → Benzeneacetyl chloride, 4-nitro-

HRID 2373744Notes

Reaction equation

HRID 2373744 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[N+:7]([C:10]1[CH:15]=[CH:14][C:13](CC(O)=O)=[CH:12][CH:11]=1)([O-:9])=[O:8].CN(C=O)C>ClCCl>[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([CH2:1][C:2]([Cl:4])=[O:3])=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 4661(4-Nitrophenyl)acetic acidHCID 6228DimethylformamideHCID 65578Oxalyl chloride

Product 1

HCID 6452210Benzeneacetyl chloride, 4-nitro-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.75 ml (7.5 mmoles) of a 2M solution of oxalyl chloride in dichloromethane is added at 20° C. to a solution of 0.9 g (5 mmoles) of 4-nitrophenylacetic acid in a mixture composed of 10 ml of dichloromethane and 0.5 ml of DMF. After agitation for 30 minutes, the solution is concentrated under vacuum. The yellow oil obtained is used without additional purification in the following stage.

Workup

  1. concentrationthe solution is concentrated under vacuum
  2. customThe yellow oil obtained
  3. customis used without additional purification in the following stage

Sources & evidence

ORD record
ord-66026f39b9844dd29ff6e7cda8b2ac86
Source dataset
uspto-grants-2008_12
Patent number
US07459558B2

Reaction notes

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