Acetophenone → 1-Phenylethanol

HRID 467331Notes

Reaction equation

HRID 467331 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2]>C(OCC)C>[CH3:2][CH:1]([OH:3])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 7410Acetophenone

Product 1

HCID 74091-PhenylethanolYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following the set-up of Example 5 and under a nitrogen atmosphere, acetophenone (2.9 g, 3.0 mL, 25 mmol) was added to a solution of B-chlorodiiso-2-ethylapopinocampheylborane (9.6 g, 27.5 mmol) in EE (ethyl ether, 20 mL) at -25° C. The reaction was complete in 48 h (followed by 11B NMR after methanolysis of an aliquot). The reaction was worked up following the procedure of Example 3 to obtain 2.2 g, 72% of α-phenethyl alcohol which was found to be of ≥99% ee by capillary GC analysis of its MTPA ester.

Sources & evidence

ORD record
ord-1760510e71e4488793f110a0eec8b97a
Source dataset
uspto-grants-1992_10
Patent number
US05159116

Reaction notes

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