Benzenepropanal, alpha,alpha-dimethyl- → 2,2-Dimethyl-3-phenylpropanol

HRID 1154503Notes

Reaction equation

HRID 1154503 reaction equation
[CH3:1][C:2]([CH3:12])([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:3]=[O:4].[H][H]>[Cr]([O-])([O-])=O.[Cu+2]>[CH3:1][C:2]([CH3:12])([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 70520Benzenepropanal, alpha,alpha-dimethyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 833672,2-Dimethyl-3-phenylpropanolYield 90%

Reagents, catalysts & solvents 1

HCID 178505374HCID 178505374, compoundCatalyst

Procedure

354 g 2,2-dimethyl-3-phenyl-propanal (1a) was hydrogenated in an autoclave with 2 g copper chromite (G-79) at 150° C. and 120 bar until it had absorbed 1 equivalent of hydrogen. When the pressure had been released in the autoclave the catalyst was separated off. Distillation on a 60 cm packed column yielded 320 g (90%) 2,2-dimethyl-3-phenyl-propanal (1b) in the form of a colourless, viscous oil. bp (2 mm)=90° C., mp. 34°-36° C. --NMR (CCl4): δ-0.88, s, 6H (2,2--CH3), 2.55, s (CH2 --3), 3.37, s (CH2 --1), 7.1-7.3, br.s (phenyl--H). --IR: 3400 cm-1 (O--H). --MS: m/e (%)=164 (16, M+), 133 (5), 131 (4), 117 (6), 115 (8), 105 (4), 92 (100), 91 (83). C11H16O (164.2).

Workup

  1. customwas separated off
  2. distillationDistillation on a 60 cm

Sources & evidence

ORD record
ord-3a466253f4ac442690051840e551f8b2
Source dataset
uspto-grants-1984_12
Patent number
US04490284

Reaction notes

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