4-Chlorobutyryl chloride → Ethyl 4-(4-chloro-1-oxobutyl)-alpha,alpha-dimethylbenzeneacetate

HRID 895031Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:12][C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(=S)=S>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:23]1[CH:24]=[CH:25][C:20]([C:13]([CH3:12])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:21][CH:22]=1)=[O:6]

Participants

Conditions

Temperature: -10 °C

Procedure

To 700 ml of carbon disulfide containing 36.5 g (0.254 mole) of 4-chlorobutyryl chloride is added 74.5 g (0.56 mole) of aluminum chloride with stirring in an ice bath (about -10° C.). Stirring is continued for about 15 minutes at about 25° C. then the mixture is recooled to 5° C. and 48.4 g (0.294 mole) of ethyl α,α-dimethylphenylacetate in 100 ml of carbon disulfide is added. The reaction mixture is stirred on an ice bath for 31/2 hours then stirred for 151/2 hours at 25° C. then poured into HCl-ice water and extracted with chloroform. The extract is washed with dilute sodium carbonate solution, water and saturated sodium chloride solution, dried over magnesium sulfate, and evaporated giving as a solid ethyl 4-(4-chloro-1-oxobutyl)-α,α-dimethylphenylacetate.

Workup

stirringStirring
customis recooled to 5° C.
stirringThe reaction mixture is stirred on an ice bath for 31/2 hours
stirringthen stirred for 151/2 hours at 25° C.
extractionextracted with chloroform
washThe extract is washed with dilute sodium carbonate solution, water and saturated sodium chloride solution
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-d8706b82d26e4cf6a77c9e418341d22c
Source dataset: uspto-grants-1981_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04285958

Reaction notes

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