HCID 86731812, compound → HCID 86731811, compound

HRID 1527824Notes

Reaction equation

HRID 1527824 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][C:6]([C:8](=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[O:14])=[CH:5][CH2:4][CH2:3]1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:16])[CH2:7][C:6]([C:8](=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:5][CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 86731812HCID 86731812, compound

Product 1

HCID 86731811HCID 86731811, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

6-(5,5-dimethylcyclohex-1-en-1-yl)-6-oxohexanal (6.67 g, 0.03 mol.), toluene (20 g, 300 wt. %) and (ethylenediamine)[1,2-bis(diphenylphosphino)ethane]ruthenium (bispivalate) (2.3 mg, 0.003 mmol, 0.01 mol.%) were loaded altogether in a 125 ml autoclave equipped with a mechanical stirring device. Sealed autoclave was then purged under stirring with nitrogen (3 times 5 bars) and hydrogen (3 times 5 bars) before being pressurized to 50 bars hydrogen. It was then heated to 100° C. and hydrogen pressure was maintained to 50 bars during all the reaction to afford desired product with 97.5% selectivity. Upon reaction completion (checked by both hydrogen consumption and GC), autoclave was then cooled down to 25° C. It was then depressurized and purged with nitrogen (3 times 5 bars) and reaction mixture was then transferred to a round-bottomed flask and solvent was removed under vacuum. After flash chromatography, 1-(5,5-dimethylcyclohex-1-en-1-yl)-6-hydroxyhexan-1-one was obtained in 93% yield.

Workup

  1. customequipped with a mechanical stirring device
  2. customSealed autoclave
  3. customwas then purged
  4. temperaturehydrogen pressure was maintained to 50 bars during all
  5. customthe reaction

Sources & evidence

ORD record
ord-f567cddda4104820b150aaad4dc6367d
Source dataset
uspto-grants-2015_07
Patent number
US09090534B2

Reaction notes

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