Acetophenone → 1-Phenylethanol

HRID 2041863Notes

Reaction equation

HRID 2041863 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O(C(C)(C)C)[Na].[C:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:28])[CH3:27]>C(O)(C)C>[CH3:27][CH:26]([OH:28])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 11776TriphenylphosphineHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 74091-Phenylethanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
30 °C

Procedure

Into a 100-mL stainless-steel autoclave was put 24.0 mg (0.03 mmol) of [CuCl((R,R)-SKEWPHOS)(PPh3)]n obtained in Example 27, triphenyl phosphine of the amount shown in Table 6 below, and 28.8 mg (0.30 mmol) of NaO-t-Bu, followed by replacing with nitrogen in the autoclave, and then 2.0 mL of isopropyl alcohol and 1.05 mL (9.0 mmol) of acetophenone were added. The reaction was carried out with stirring under a hydrogen pressure of 5 MPa at 30° C. for 16 to 17 hours to give 1-phenethyl alcohol which is a hydrogenated compound of acetophenone. The reaction mixture was analyzed by using GC. The results are shown in Table 6.

Sources & evidence

ORD record
ord-9b80b65d23f342a29b7eb8d5ce0d5022
Source dataset
uspto-grants-2013_11
Patent number
US08586498B2

Reaction notes

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