Oxygen → HCID 1549372, compound

HRID 327847Notes

Reaction equation

HRID 327847 reaction equation
O=O.[C:3]([C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[C:14](\[CH3:17])/[CH2:15][OH:16])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4]>C1(C)C=CC=CC=1>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C@@H:14]([CH3:17])[CH2:15][OH:16])=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 977OxygenHCID 10584344HCID 10584344, compound

Product 1

HCID 1549372HCID 1549372, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 500 ml autoclave was charged in a glove box (O2 content <1 ppm) with 16.11 g (78.85 mmol) of (E)-3-(4-tert.butylphenyl)-2-methylprop-2-en-1-ol, 145 ml of toluene and 5 ml of catalyst solution (in accordance with a)). This mixture was hydrogenated at 100°, a constant pressure of 60 bar H2 and while stirring intensively. The conversion was >99% after 22 hours. The pale yellow hydrogenation solution was rinsed from the autoclave and evaporated on a rotary evaporator at 60°/17 mbar. The residue was distilled at 140°/0.01 mbar. There were obtained 16.0 g (99.0%) of (R)-3-(4-tert.butylphenyl)-2-methylpropan-1-ol as a colourless oil with an enantiomeric purity of 91.3% e.e.

Workup

  1. customwas hydrogenated at 100°
  2. customafter 22 hours
  3. washThe pale yellow hydrogenation solution was rinsed from the autoclave
  4. customevaporated on a rotary evaporator at 60°/17 mbar
  5. distillationThe residue was distilled at 140°/0.01 mbar

Sources & evidence

ORD record
ord-74be0e55943a49809a800b98f8d56d4a
Source dataset
uspto-grants-1993_12
Patent number
US05274125

Reaction notes

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