Oxalyl chloride → 4-Cyano-3-methylbenzoyl chloride

HRID 587837Notes

Reaction equation

HRID 587837 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][C:4]=1[CH3:12])#[N:2].C(Cl)(=O)C([Cl:16])=O>ClCCl.CN(C)C=O>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:16])=[O:8])=[CH:5][C:4]=1[CH3:12])#[N:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 102410994-Cyano-3-methylbenzoic acid

Product 1

HCID 866666194-Cyano-3-methylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The crude product of 4-cyano-3-methylbenzoic acid (1.0 g) was suspended in dichloromethane. To the mixture, oxalyl chloride (1.2 g) and an catalytic amount of N,N-dimethylformamide (2 to 3 drops) were added under ice cooling. After adjusting to room temperature, the reaction solution was stirred for three hours. The solvent was distilled off under reduced pressure to obtain 4-cyano-3-methylbenzoyl chloride as a crude product (1.0 g).

Workup

  1. customAfter adjusting to room temperature
  2. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f76b591967314e72a880ffa16a0e1c45
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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