Sulfuric Acid → 1-[1-(4-Chlorophenyl)cyclobutyl]-2-methoxyethanone

HRID 1650970Notes

Reaction equation

HRID 1650970 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([O:17]C)(OC)[CH2:13][OH:14])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:19]I.[OH-].[K+].S(=O)(=O)(O)O>O.CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](=[O:17])[CH2:13][O:14][CH3:19])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 198237812-[1-(4-Chlorophenyl)cyclobutyl]-2,2-dimethoxyethanol

Product 1

HCID 198236811-[1-(4-Chlorophenyl)cyclobutyl]-2-methoxyethanone

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2-[1-(4-Chlorophenyl)cyclobutyl]-2,2-dimethoxyethanol (1.48 g) and then methyl iodide (1.86 g) were added to a mixture of powdered potassium hydroxide (1.23 g) and dry dimethylsulphoxide (10 ml) which had been stirred for 5 minutes. The mixture was stirred for 30 minutes and was then poured into water (100 ml). The resulting mixture was acidified with concentrated sulphuric acid and extracted with dichloromethane. The extract was washed with water and dried and then evaporated to give 1-[1-(4-chlorophenyl)cyclobutyl]-2-methoxyethanone as an oil.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-3c644098fede480fb6a1f9064e60288d
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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