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

HRID 2294656Notes

Reaction equation

HRID 2294656 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 mol), 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-b470bf5345b645b7873d436af432c70b
Source dataset
uspto-grants-1997_11
Patent number
US05689000

Reaction notes

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