Benzoyl chloride, 3-nitro- → HCID 16876476, compound

HRID 1974001Notes

Reaction equation

HRID 1974001 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](Cl)=[O:18])([O-:13])=[O:12].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:17]([C:16]1[CH:20]=[CH:21][CH:22]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=1)=[O:18]

Participants

5

Reactant 3

HCID 8495Benzoyl chloride, 3-nitro-HCID 90161,4-DimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 16876476HCID 16876476, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 1.6 l of methylene chloride was dissolved 280 g of p-dimethoxybenzene and 372 g of m-nitrobenzoyl chloride. In this solution 300 g of aluminum chloride was added with stirring. After being allowed to stand overnight, the mixture was poured into ice water and the organic liquid phase was separated. After the methylene chloride was removed by distillation, the residual product was recrystallized from ethanol to obtain 470 g of pale yellow crystals of the subject compound which had a melting point of 98° C.

Workup

  1. customthe organic liquid phase was separated
  2. customAfter the methylene chloride was removed by distillation
  3. customthe residual product was recrystallized from ethanol

Sources & evidence

ORD record
ord-d9a383b8103d4fd89ef2ab22d4e2ab98
Source dataset
uspto-grants-1976_12
Patent number
US03999991

Reaction notes

Loading…