Ethanol → 1-Phenylethanol

HRID 917900Notes

Reaction equation

HRID 917900 reaction equation
P.[C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:4])[CH3:3].C(O)C>O>[CH3:3][CH:2]([OH:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 7410AcetophenoneHCID 24404Phosphine

Product 1

HCID 74091-Phenylethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Into a 3 ounce glass pressure bottle are placed 180 milligrams of [Rh(norbornadiene) (iso-propylphenylmethylphosphine)2 ]BF4 ([α]D25 = +11.0° for the phosphine), 7.7 grams of acetophenone, 3 ml absolute ethanol, and 0.12 ml water. The bottle is flushed and filled with hydrogen as in Example 1 to 30 psig. The bottle is warmed to 60°C and the contents stirred for 5 hours. Distillation of the reaction mass affords pure α-methylbenzyl alcohol, [α]D25 = -1.78°, optical purity = 4.2%.

Workup

  1. customThe bottle is flushed
  2. distillationDistillation of the reaction mass

Sources & evidence

ORD record
ord-51efbe8de474488896d56775330223ba
Source dataset
uspto-grants-1976_07
Patent number
US03968147

Reaction notes

Loading…