Sodium borohydride → 2-Methyl-3-[4-(2-methylbutan-2-yl)phenyl]prop-2-en-1-ol

HRID 1395212Notes

Reaction equation

HRID 1395212 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

HCID 4311764Sodium borohydrideHCID 533951972-Methyl-3-[4-(2-methylbutan-2-yl)phenyl]prop-2-enal

Product 1

HCID 572455772-Methyl-3-[4-(2-methylbutan-2-yl)phenyl]prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. additiontreated portionwise
  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-d2c9e9ad6635480babf7f33bfdf149e6
Source dataset
uspto-grants-1980_05
Patent number
US04202894

Reaction notes

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