Sodium borohydride → 2-Methyl-3-[4-(2-methylbutan-2-yl)phenyl]prop-2-en-1-ol
Reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[C:13]([CH3:16])[CH:14]=[O:15])=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]=[C:13]([CH3:16])[CH2:14][OH:15])=[CH:10][CH:11]=1)([CH2:4][CH3:5])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
432.62 g of 3-(p-tert.amyl -phenyl)-2-methyl-acrolein are dissolved in 2500 ml of methanol and treated portionwise while cooling with ice with 38 g of sodium borohydride. Subsequently, the mixture is stirred at room temperature for 2.5 hours, poured into 2500 ml of ice-cold 2-N hydrochloric acid and exhaustively extracted with hexane. The combined hexane extracts are washed neutral with water, dried over sodium sulphate and evaporated. Vacuum distillation yields pure 3-(p-tert.amyl-phenyl)-2-methyl-allyl alcohol of boiling point 128°-133° C./0.04 Torr.