HCID 67179295, compound → HCID 67179717, compound

HRID 1045068Notes

Reaction equation

HRID 1045068 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[C:5]1[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][CH2:6]1>C(OCC)(=O)C.CO.[Pd]>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH:5]1[CH2:10][CH2:9][C:8]([CH3:11])([CH3:12])[CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 67179295HCID 67179295, compound

Product 1

HCID 67179717HCID 67179717, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a stirred solution of the above alkene (100 mg, 0.54 mmol) in a mixture of ethyl acetate-methanol (0.8 mL, 1:1) was added Pd—C (10 mg, 20% on activated carbon) and the resultant mixture was stirred under hydrogen pressure (50 psi) for 2 h in a resealable glass pressure vessel equipped with a manometer and pressure valve. The catalyst was filtered off using a pad of Celite® and the Celite® pad was washed with an ethyl acetate-methanol mixture (1:1, about 10 mL). The combined filtrate was concentrated under reduced pressure to give the desired (4,4-dimethyl-cyclohexyl)-acetic acid methyl ester (80 mg).

Workup

  1. customequipped with a manometer and pressure valve
  2. filtrationThe catalyst was filtered off
  3. washthe Celite® pad was washed with an ethyl acetate-methanol mixture (1:1, about 10 mL)
  4. concentrationThe combined filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7368811a439415091e89b6d56799e67
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

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