3-Phenylprop-2-En-1-Ol → Benzenepropanol

HRID 1779284Notes

Reaction equation

HRID 1779284 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+:12].[OH2:13]>[Ni]>[C:4]1([CH2:3][CH2:2][C:1]([O-:11])=[O:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Na+:12].[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.[Na+:12]

Participants

7

Reactant 3

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

Product 3

HCID 31234BenzenepropanolHCID 517055Sodium BenzoateHCID 19205590HCID 19205590, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Into a 300 ml nickel autoclave are charged cinnamyl alcohol (50.0 g, 0.37 mo1), sodium hydroxide (34.6 g, 0.43 mol), the catalyst of Example 2 (12.8 g catalyst suspended in 48.6 g water) and water (75 g). The autoclave is sealed and purged with nitrogen. The autoclave is heated under pressure of 1.0×106Pascals to 170° C. After hydrogen evolution ceases, the reaction product filtered and the basic filtrate is extracted with diethylether. The aqueous phase is acidified and extracted with ether. The acid and base extracts are evaporated and analyzed. The reaction yields sodium 3-phenylpropionate (69 mol percent), 3-phenylpropanol (25 mol percent) and sodium benzoate (8 mol percent).

Workup

  1. customThe autoclave is sealed
  2. custompurged with nitrogen
  3. temperatureThe autoclave is heated under pressure of 1.0×106Pascals to 170° C
  4. filtrationAfter hydrogen evolution ceases, the reaction product filtered
  5. extractionthe basic filtrate is extracted with diethylether
  6. extractionextracted with ether
  7. customThe acid and base extracts are evaporated

Sources & evidence

ORD record
ord-031403b8500a44c389860f15a67db092
Source dataset
uspto-grants-1997_05
Patent number
US05627125

Reaction notes

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