Acetophenone → 1-Phenylethanol

HRID 2289179Notes

Reaction equation

HRID 2289179 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2]>C1COCC1>[C:4]1([CH:1]([OH:3])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 7410Acetophenone2×

Product 1

HCID 74091-PhenylethanolYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaAlH[(S)-BINOL](OMe) gave surprisingly and unexpectedly high conversion (chemical yield) and enantioselectivity values relative to LiAlH[(S)-BINOL](OMe), when admixed with acetophenone (AP). In a comparative experiment, NaAlH[(S)-BINOL](OMe) was admixed with AP in THF at -70° C. to afford 79% 1-phenylethanol (PET) with the (S)-enantiomer in 97% enantiomeric excess, whereas under similar conditions, LiAlH((R)-BINOL)(OMe) afforded only 60% PET with the (R)-enantiomer in only 87% enantiomeric excess (J. Am. Chem. Soc., 1984, 106, 6709). Thus, NaAlH[(S)-BINOL](OMe) is surprisingly and unexpectedly a more efficient and enantioselective reducing agent than its lithium analog.

Sources & evidence

ORD record
ord-2bf90cd255fc4f8ab7d8eebad8933c08
Source dataset
uspto-grants-2000_07
Patent number
US06090950

Reaction notes

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