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

HRID 863459Notes

Reaction equation

HRID 863459 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:16])=O>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([Cl:16])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 4661(4-Nitrophenyl)acetic acidHCID 24386Thionyl Chloride

Product 1

HCID 6452210Benzeneacetyl chloride, 4-nitro-Yield 100%

Procedure

A stirred mixture of 4-nitrophenylacetic acid (25 g, 0.138 mol) in thionyl chloride (50 ml, 0.685 mol) was heated at reflux for 2 hours then concentrated to yield 4-nitrophenylacetyl chloride (27.55 g) as a tan solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. concentrationthen concentrated

Sources & evidence

ORD record
ord-cdd0f989aed84df599d7a26af99cf41d
Source dataset
uspto-grants-1998_02
Patent number
US05721247

Reaction notes

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