Toluene → 3-t-Butyl-5-cyano-4-methoxybenzoyl chloride

HRID 385034Notes

Reaction equation

HRID 385034 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:16]#[N:17])[C:13]=1[O:14][CH3:15])[C:8](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.S(Cl)([Cl:27])=O>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:16]#[N:17])[C:13]=1[O:14][CH3:15])[C:8]([Cl:27])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 681088003-t-Butyl-5-cyano-4-methoxybenzoic acid

Product 1

HCID 866681523-t-Butyl-5-cyano-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3-t-butyl-5-cyano-4-methoxybenzoic acid (586 mg), toluene (10 mL), N,N-dimethylformamide (2 droplets) and thionyl chloride (0.27 mL) was added, and the mixture was stirred at 60° C. for 16 hours. The solvent was distilled off under reduced pressure and then azeotroped with toluene to obtain the title compound (630 mg) as a brown oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-ab39d87e500949cc8acb8858fd035b3d
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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