Hydrochloric Acid → 4-(4-Methylphenyl)butan-2-ol

HRID 840997Notes

Reaction equation

HRID 840997 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([OH:12])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Procedure

A solution of 1-(4-methylphenyl)butan-3-one (11.4 g, 70.3 mmol) in methanol (80 ml) was cooled, followed by adding thereto sodium tetrahydroborate (1.51 g, 40.0 mmol), and the resulting mixture was stirred at 0° C. for 2 hours. The reaction mixture was added to 1N hydrochloric acid, and the methanol was distilled off under reduced pressure and the residue was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 11.7 g of 1-(4-methylphenyl)butan-3-ol.

Workup

  1. additionby adding
  2. distillationthe methanol was distilled off under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe extract solution was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5eb543cb27fb44b0b542c21fdd42519d
Source dataset
uspto-grants-2002_04
Patent number
US06369110B1

Reaction notes

Loading…