Benzeneacetic acid, 4-hydroxy-, methyl ester → Methyl 2-(4-oxocyclohexyl)acetate

HRID 1047356Notes

Reaction equation

HRID 1047356 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[H][H]>[Pd].CC1C=CC=CC=1C>[CH3:12][O:11][C:9]([CH2:8][CH:5]1[CH2:6][CH2:7][C:2](=[O:1])[CH2:3][CH2:4]1)=[O:10]

Participants

5

Reactant 2

HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 21249113Methyl 2-(4-oxocyclohexyl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

A high pressure autoclave was charged with a mixture of methyl (4-hydroxyphenyl)acetate (50 g, 0.30 mol), palladium (5 g) (10%) on carbon (50% wet) and O-xylene (250 mL). The reaction mixture was stirred under 110 to 115 psi of hydrogen pressure for 7 to 8 h at 140° C. The reaction was monitored by HPLC. The reaction mixture was then cooled to room temperature, and the catalyst was filtered off. Filtrate was concentrated under reduced pressure to get 4-(methoxycarbonylmethyl)cyclohexanone as light yellow to colorless oily liquid (48.7 g, 97.4%).

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationFiltrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6ec73662b27c418eaff9c7d4231747e1
Source dataset
uspto-grants-2013_10
Patent number
US08569519B2

Reaction notes

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