Benzoyl chloride → 4-(3-Benzoyl-4-methoxyphenyl)-2-butanone

HRID 1074571Notes

Reaction equation

HRID 1074571 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[C:14]([C:4]1[CH:5]=[C:6]([CH2:9][CH2:10][C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 61007AnisylacetoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 204960374-(3-Benzoyl-4-methoxyphenyl)-2-butanoneYield 49.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-(4-methoxyphenyl)-2-butanone (15.4 g.), benzoyl chloride (13 g.) and methylene chloride (250 ml) at 0° C. was added portionwise aluminium chloride (23 g.) over a 20 minute period. The mixture was stirred a further 1 hour at room temperature and then poured onto ice and worked up in the usual way. Distillation of the product gave 4-(3-benzoyl-4-methoxyphenyl)-2-butanone (12 g.), b.p. 188°-192° C. (0.01 mm).

Workup

  1. additionpoured onto ice
  2. distillationDistillation of the product

Sources & evidence

ORD record
ord-e336def680134552895240deed2741ac
Source dataset
uspto-grants-1983_07
Patent number
US04393079

Reaction notes

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