HCID 12148781, compound → HCID 12148782, compound

HRID 902578Notes

Reaction equation

HRID 902578 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH:4]([C:6]12[CH2:11][CH:10]1[CH2:9][CH2:8][CH2:7]2)[OH:5]>CCOCC.[O-2].[Mn+4].[O-2]>[CH3:1][O:2][C:3](=[O:12])[C:4]([C:6]12[CH2:11][CH:10]1[CH2:9][CH2:8][CH2:7]2)=[O:5]

Participants

4

Reactant 1

HCID 12148781HCID 12148781, compound

Product 1

HCID 12148782HCID 12148782, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

2×40 g active manganese(IV)oxide were added one after the other over 2 hours to a well-stirred solution of 13.6 g (80 mmol) 2-(bicyclo[3.1.0]hex-1-yl)-2-hydroxyacetic acid methyl ester in 500 ml anhydrous ether, and the mixture was stirred at room temperature for a further 4 hours until all the starting material was used up (DC control). The reaction mixture was then filtered over diatomaceous earth (Celite®). After the solvent was evaporated off in vacuum at room temperature, 10.8 g (80%) of 2-(bicyclo[3.1.0]hex-1-yl)-2-oxoacetic acid methyl ester was obtained as clear light-yellow liquid (purity >96% according to GC), which does not have to be purified further.

Workup

  1. filtrationThe reaction mixture was then filtered over diatomaceous earth (Celite®)
  2. customAfter the solvent was evaporated off in vacuum at room temperature

Sources & evidence

ORD record
ord-d66c7510938e4d96a6586b02d4ea3c9a
Source dataset
uspto-grants-2008_04
Patent number
US07365222B2

Reaction notes

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