HCID 20226191, compound → 1-(2,2,3,6-Tetramethylcyclohexyl)hexan-3-ol

HRID 1248874Notes

Reaction equation

HRID 1248874 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:7]([CH3:8])[CH2:6][CH2:5][CH:4]([CH3:9])[C:3]1=[C:10]=[CH:11][CH:12]([OH:16])[CH2:13][CH2:14][CH3:15].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:17][C:2]1([CH3:1])[CH:7]([CH3:8])[CH2:6][CH2:5][CH:4]([CH3:9])[CH:3]1[CH2:10][CH2:11][CH:12]([OH:16])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 20226191HCID 20226191, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 223261871-(2,2,3,6-Tetramethylcyclohexyl)hexan-3-olYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2 G (8.5 mM) of 1-(2,2,3,6-tetramethyl-1-cyclohexylidene)-1-hexen-3-ol in 20 ml of ethyl acetate were hydrogenated in the presence of 0.2 g of palladium at 5% on charcoal, in an autoclave containing a hydrogen atmosphere maintained at a pressure of 100 atm. After filtration, the mixture was concentrated and distilled by means of a bulb apparatus (bath temp.: about 130°) under reduced pressure. There were thus obtained 1.9 g (yield 95%) of a mixture containing about 80% by weight of 1-(2,2,c-3,t-6-tetramethyl-r-1-cyclohexyl)-3-hexanol and 10% of 1-(2,2,t-3,c-6-tetramethyl-r-1-cyclohexyl)-3-hexanol accompanied by minor amounts of 1-(2,2,c-3,c-6-tetramethyl-r-1-cyclohexyl)-3-hexanol and 1-(2,2,t-3,t-6-tetramethyl-r-1-cyclohexyl)-3-hexanol.

Workup

  1. temperaturemaintained at a pressure of 100 atm
  2. filtrationAfter filtration
  3. concentrationthe mixture was concentrated
  4. distillationdistilled by means of a bulb apparatus (bath temp.: about 130°) under reduced pressure

Sources & evidence

ORD record
ord-650f8cec93d8426591a3d1730a731e87
Source dataset
uspto-grants-1986_12
Patent number
US04626602

Reaction notes

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