Oxygen → (S)-2-methyl-3-phenylpropan-1-ol

HRID 1975864Notes

Reaction equation

HRID 1975864 reaction equation
O=O.[CH3:3]/[C:4](=[CH:7]\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)/[CH2:5][OH:6]>C1(C)C=CC=CC=1>[CH3:3][C@@H:4]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 977OxygenHCID 6393846alpha-Methylcinnamic alcohol

Product 1

HCID 11804940(S)-2-methyl-3-phenylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In a glove box (O2 content<1 ppm), a catalyst solution is prepared by dissolving 9.15 mg (0.0186 mmol) of dichloro-bis(1,5-cyclooctadiene)dirhodium and 25.18 mg (0.0371 mmol) of (R)-p-TolBINAP in 50 ml of toluene. This catalyst solution is then added to a solution of 5.5 g (37.1 mmol) of (E)-2-methyl-3-phenyl-2-propen-1-ol in 35 ml of toluene in a 500 ml autoclave. The hydrogenation is carried out at 100° C. under a constant pressure of 60 bar and with efficient stirring. The conversion is 100% after 22 hours. The pale yellow hydrogenation solution is worked up as described in Example 2, giving (S)-2-methyl-3-phenylpropan-1-ol in an enantiomeric purity of 89.1% e.e.

Workup

  1. customis carried out at 100° C. under a constant pressure of 60 bar and with efficient stirring
  2. customafter 22 hours

Sources & evidence

ORD record
ord-f0eb083d4fdc434d9c5d4756d12e05a0
Source dataset
uspto-grants-1994_02
Patent number
US05288928

Reaction notes

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