Dimethylformamide → p-Anisoyl chloride

HRID 261406Notes

Reaction equation

HRID 261406 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.S(Cl)([Cl:14])=O.CN(C)C=O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:14])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 74784-Methoxybenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 7477p-Anisoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A slurry of 22.5 g. (0.15 mole of 4-methoxybenzoic acid in benzene at reflux is treated with 12.5 ml. (0.15 mole) of thionyl chloride and 1 ml. of N,N-dimehtyl formamide. After stirring for 15 minutes the solution is evaporated and cooled to provide 4methoxybenzoyl chloride as a yellow solid. The solid is dissolved in carbon disulfide and added to 20 g. (0.15 mole) of aluminum chloride slurried in 200 ml. of carbon sulfide. To this mixture is added 30 g. (0.15 mole) of 2,6-di(t-butyl)phenol. After stirring for two hours at room termperature, the resulting mixture is poured into a dilute hydrochloric acid-ice mixture, then extracted with three portions of dichloromethane. The organic layer is dried, then evaporated to provide a residue which is recrystallized twice from a benzene-hexane mixture to provide 4-(4-methoxybenzoyl)-2,6-di(t-butyl)phenol, m.p. 141°-142.5° C.

Workup

  1. additionis treated with 12.5 ml
  2. customis evaporated
  3. temperaturecooled

Sources & evidence

ORD record
ord-875ad5324ff244a8855fbd574cbc0c44
Source dataset
uspto-grants-1979_08
Patent number
US04165383

Reaction notes

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