Acetophenone → 1-Phenylethanol

HRID 1838775Notes

Reaction equation

HRID 1838775 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[H][H]>C1CCCCC1>[C:4]1([CH:1]([OH:3])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 7410AcetophenoneHCID 178418361HCID 178418361, compound2×

Product 2

HCID 74091-PhenylethanolYield 81%HCID 7500EthylbenzeneYield 19%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
120 °C

Procedure

For Example E15 according to the present invention, the above-described 300 ml autoclave provided with a metal basket fastened to the lid of the autoclave, as used in Example E6 to E12, was employed; in the present example, the metal basket was used for accommodating 9.2 g of the catalyst IC11 (wire mesh rings). In its center, the basket had a cylindrical opening for the shaft of the stirrer, so that the catalyst was supplied uniformly with liquid and gas. The autoclave was charged with 200 ml of cylcohexane and 8 g of acetophenone, closed and freed of air by pressurizing it twice to 100 bar with nitrogen. The autoclave was subsequently heated to 120° C. and 250 bar of hydrogen were injected. While injecting further hydrogen to replace that consumed, the mixture was stirred for a further 60 minutes at this temperature. A total of 1.59 liters of hydrogen were consumed. Analysis of the resulting product by gas chromatography indicated complete conversion of the acetophenone to form 1-phenylethanol (81%) and ethylbenzene (19%).

Workup

  1. customthe above-described 300 ml autoclave provided with a metal basket
  2. customclosed
  3. customA total of 1.59 liters of hydrogen were consumed

Sources & evidence

ORD record
ord-7506daef1b874185b2641e9b451263aa
Source dataset
uspto-grants-2004_01
Patent number
US06676919B1

Reaction notes

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