Oxygen → HCID 1715217, compound

HRID 1647353Notes

Reaction equation

HRID 1647353 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 1715217HCID 1715217, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A catalyst solution was prepared in a 50 ml of measuring flask in a glove box (O2 content <1 ppm) by dissolving 9.7 mg (0.02 mmol) of dichloro-bis-(1,5-cyclooctadiene)dirhodium and 21.9 mg (0.04 mMol) (R)-HOBIPHEP in 50 ml of toluene. 5 ml of this catalyst solution were added to a solution of 16.1 g (78.85 mmol) of (E)-3-(p-tert.butylphenyl)-2-methyl-2-propen1-ol [(E)-dehydroliliol] in 145 ml of toluene in a 500 ml autoclave. The hydrogenation was carried out at 100° , a constant pressure of 60 bar and while stirring intensively. The conversion was 99.9% after 21 hours. The pale yellow hydrogenation solution was rinsed from the autoclave and evaporated at 60°/17 mbar on a rotary evaporator. The residue was distilled at 140°/0.01 mbar. There were obtained 16.1 g (99.0%) of (S) -3-(p-tert.butylphenyl)-2-methyl-1-propanol [(S)-liliol], as a colourless oil with an enantiomeric purity of 96.2% e.e.

Workup

  1. customA catalyst solution was prepared in a 50 ml
  2. customwas carried out at 100°
  3. customafter 21 hours
  4. washThe pale yellow hydrogenation solution was rinsed from the autoclave
  5. customevaporated at 60°/17 mbar
  6. customon a rotary evaporator
  7. distillationThe residue was distilled at 140°/0.01 mbar

Sources & evidence

ORD record
ord-4c00ac887b0f4f29bbc3c13f7f200cda
Source dataset
uspto-grants-1995_07
Patent number
US05430191

Reaction notes

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