2-Propenal, 3-[4-(1,1-dimethylethyl)phenyl]-2-methyl- → 3-(4-tert-Butylphenyl)-2-methylprop-2-en-1-ol

HRID 1733273

Reaction equation

HRID 1733273 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([CH3:15])[CH:13]=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[C:12]([CH3:15])[CH2:13][OH:14])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 1146592-Propenal, 3-[4-(1,1-dimethylethyl)phenyl]-2-methyl-HCID 4311764Sodium borohydride

Product 1

HCID 543813673-(4-tert-Butylphenyl)-2-methylprop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

404.5 g of 3-(p-tert.butyl-phenyl)-2-methyl-acrolein are dissolved in 2500 ml of methanol and treated portionwise with 38 g of sodium borohydride while cooling with ice. 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.butyl-phenyl)-2-methyl-allyl alcohol of boiling point 119° C./0.005 Torr.

Workup

  1. temperaturewhile cooling with ice
  2. extractionexhaustively extracted with hexane
  3. washThe combined hexane extracts are washed neutral with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. distillationVacuum distillation

Sources & evidence

ORD record
ord-c9b3e26ab02241aaa76378731f7f9858
Source dataset
uspto-grants-1980_12
Patent number
US04241058

Linked notes

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