Methane → HCID 13174427, compound

HRID 2166953Notes

Reaction equation

HRID 2166953 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH:5]([CH:7]1[CH2:11][C:10]([CH3:12])=[CH:9][C:8]1=[O:13])[OH:6])[CH3:2].C.[H][H]>C1(C)C=CC=CC=1.[Pd]>[CH2:1]([O:3][C:4](=[O:14])[CH:5]([OH:6])[CH:7]1[CH2:11][CH:10]([CH3:12])[CH2:9][C:8]1=[O:13])[CH3:2]

Participants

6

Reactant 3

HCID 297MethaneHCID 13174425HCID 13174425, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13174427HCID 13174427, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

Step 2, Hydrogenation Process (Ethyl Ester): 99.1 g of crude alpha-hydroxy-(4-methyl-2-oxo-3-cyclopenten-1-yl)-acetic acid ethyl ester (as prepared in Example 1) in 882 ml of toluene was hydrogenated over 9.91 g of 10% by weight of palladium and 90% by weight of charcoal at room temperature and 25-50 psi. After hydrogen uptake had ceased, the catalyst and solvent were removed by filtration and evaporation to give 101 g of a viscous, amber-colored oil. This oil is distilled to provide the product alpha-hydroxy-4-methyl-2-oxo-cyclopentane acetic acid ethyl ester, bp 96°-111°/0.05 mmHg, for use in Example 5.

Workup

  1. customthe catalyst and solvent were removed by filtration and evaporation
  2. customto give 101 g of a viscous, amber-colored oil
  3. distillationThis oil is distilled

Sources & evidence

ORD record
ord-403e75845c6f43aea55cfba886ffb68e
Source dataset
uspto-grants-1983_06
Patent number
US04390718

Reaction notes

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