Dimethylformamide → p-Anisoyl chloride

HRID 1703568Notes

Reaction equation

HRID 1703568 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-dimethyl formamide. After stirring for 15 minutes the solution is evaporated and cooled to provide 4-methoxybenzoyl 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 disulfide. To this mixture is added 30 g. (0.15 mole) of 2,6-di(t-butyl)phenol. After stirring for 2 hours at room temperature, 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-067083b3fa754b16b4ec7dbe343cb3c1
Source dataset
uspto-grants-1978_11
Patent number
US04124725

Reaction notes

Loading…