2-Phenylpropanal → 2-Phenyl-1-propanol

HRID 2367077Notes

Reaction equation

HRID 2367077 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+].[C:22]1([CH:28]([CH3:31])[CH:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[H][H]>>[C:22]1([CH:28]([CH3:31])[CH2:29][OH:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 71462-PhenylpropanalHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 142952-Phenyl-1-propanolYield 58.3%

Procedure

Into a stainless steel autoclave equipped with a glass inner tube, Cu(NO3)(PPh3)2 (11.7 mg, 0.018 mmol) and triphenylphosphine (28.3 mg, 0.108 mmol) were introduced. The inside of the autoclave was then replaced with nitrogen. To the autoclave, an ethanolic solution of sodium hydroxide (0.03 M) (6.0 mL, 0.18 mmol) and 2-phenylpropionaldehyde (1.21 mL, 9 mmol) were added, and stirring was performed at a hydrogen pressure of 5 MPa at 50° C. for 16 hours. The hydrogen was released with great care, and the conversion was analyzed by GC (95%). The contents were concentrated, and then purified by silica gel chromatography. Thus, 715 mg of 2-phenyl-1-propanol was obtained (yield: 58%).

Workup

  1. concentrationThe contents were concentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-35a4b94d19ec494a913a286a0e1d94ff
Source dataset
uspto-grants-2014_04
Patent number
US08697881B2

Reaction notes

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