Sulfuric Acid → (1-(4-Chlorophenyl)cyclobutyl)methanol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](O)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1Participants
Procedure
15.6 g of 1-(4-chlorophenyl)-cyclobutane-1-carboxylic acid, dissolved in 80 ml of absolute tetrahydrofuran, were added dropwise to 7.68 g of lithium aluminum hydride in 250 ml of absolute tetrahydrofuran at room temperature, under nitrogen. The mixture was stirred for 1 hour under reflux and for 12 hours at room temperature, after which it was hydrolyzed with ice water, acidified with 10% strength sulfuric acid and extracted with methylene chloride. The extract was dried and the solvent was evaporated to give 11.5 g of 1-(4-chlorophenyl)-1-hydroxymethylcyclobutane of melting point 53°-54° C. This was dissolved in 105 ml of pyridine in the absence of moisture, and 7.8 g of methanesulfonyl chloride were added dropwise at 0°-5° C. Stirring was continued for 2 hours at this temperature, after which the suspension was poured into ice water and extracted with methylene chloride, the combined organic phases were washed with water and dried, the solvent was removed and the product was recrystallized from cyclohexane. 5.1 g of [1-(4-chlorophenyl)-cyclobut-1-yl]-methyl methanesulfonate of melting point 66°-70° C. were obtained.
Workup
- extractionextracted with methylene chloride
- customThe extract was dried
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-6aff82a81ee645c385116124ddf74bd1
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04670454
Reaction notes
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