3-Phenylprop-2-En-1-Ol → 3-Phenylpropionate ion(1-)

HRID 2380428Notes

Reaction equation

HRID 2380428 reaction equation
[CH2:1]([OH:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-:11].[Na+].[OH2:13]>[Ni].[Cu].[Mo]>[C:4]1([CH2:3][CH2:2][C:1]([O-:11])=[O:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:4]1([CH2:3][CH2:2][CH2:1][OH:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:3]([O-:13])(=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

9

Reactant 3

HCID 3083-Phenylprop-2-En-1-OlHCID 962WaterHCID 14798Sodium Hydroxide

Product 3

HCID 242BenzoateYield 8%HCID 31234BenzenepropanolYield 25%HCID 47407003-Phenylpropionate ion(1-)Yield 69%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 23932MolybdenumCatalystHCID 23978CopperCatalyst

Conditions

Temperature
170 °C

Procedure

Into a 300 ml nickel autoclave was charged cinnamyl alcohol (50.0 g, 0.373 mol), sodium hydroxide (34.59 g, 0.432 mol) Raney copper containing about 70 ppm molybdenum (12.81 g copper suspended in 48.6 g water) and water (75 g). The autoclave was sealed and purged with nitrogen. The autoclave was heated under pressure to 170° C. for about 18 hours. The reaction products were filtered and the basic filtrate was extracted with diethyl ether. The aqueous phase was acidified and extracted with ether. The acid and base extracts were evaporated and analyzed. The reaction yielded 3-phenylpropionate (69%), 3-phenylpropanol (25%) and benzoate (8%) with 96% closure.

Workup

  1. customThe autoclave was sealed
  2. custompurged with nitrogen
  3. filtrationThe reaction products were filtered
  4. extractionthe basic filtrate was extracted with diethyl ether
  5. extractionextracted with ether
  6. customThe acid and base extracts were evaporated

Sources & evidence

ORD record
ord-f616167040ec4dcb90bcb9bb1676d01c
Source dataset
uspto-grants-1994_11
Patent number
US05367112

Reaction notes

Loading…