Acetone → α-Cyclopropyl-4-(methylthio)benzenemethanol

HRID 1087137Notes

Reaction equation

HRID 1087137 reaction equation
CO.[CH:3]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=2)=[O:7])[CH2:5][CH2:4]1.[BH4-].[Na+].CC(C)=O>C(Cl)(Cl)Cl>[CH:3]1([CH:6]([OH:7])[C:8]2[CH:9]=[CH:10][C:11]([S:14][CH3:15])=[CH:12][CH:13]=2)[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 4311764Sodium borohydrideHCID 13533274Cyclopropyl[4-(methylsulfanyl)phenyl]methanone

Product 1

HCID 14988329α-Cyclopropyl-4-(methylthio)benzenemethanolYield 74.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 200 ml of methanol solution containing 24 g of cyclopropyl (4-methylthiophenyl)ketone was added slowly 9.4 g of sodium borohydride under an ice-cooled condition, the reaction mixture was stirred for 2 hours. Then an adequate amount of acetone was added to the reaction mixture and concentrated under a reduced pressure. To the residue thus obtained was added chloroform, and the chloroform solution was washed with water, dried with anhydrous sodium sulfate, and the solvent was removed by evaporation to yield 18 g of 1-(cyclopropyl, hydroxylmethyl)-4-methylthiobenzene as in the form of colorless oily substance.

Workup

  1. temperaturecooled condition
  2. concentrationconcentrated under a reduced pressure
  3. customTo the residue thus obtained
  4. washthe chloroform solution was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-5ffa4fc8c9e247ef9ec4b4a7180722be
Source dataset
uspto-grants-1991_07
Patent number
US05034395

Reaction notes

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