Diethyl Oxalate → Ethyl 2-oxo-2-(2-oxocyclohexyl)acetate

HRID 2064642Notes

Reaction equation

HRID 2064642 reaction equation
[Na].[C:2]([O:9][CH2:10][CH3:11])(=[O:8])[C:3]([O:5]CC)=O.[C:12]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(O)C>[CH2:10]([O:9][C:2](=[O:8])[C:3](=[O:5])[CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C:12]1=[O:18])[CH3:11]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 7967CyclohexanoneHCID 5360545Sodium

Product 1

HCID 219637Ethyl 2-oxo-2-(2-oxocyclohexyl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of sodium (1.75 g) in ethanol (100 ml) was treated with a mixture of diethyl oxalate (9.41 ml) and cyclohexanone (7.18 ml). The mixture was heated to 60° C. for 5 hours then cooled and then evaporated to yield oxo-(2-oxo-cyclohexyl)-acetic acid ethyl ester as a brown foam (16.635 g). LC-MS (METHOD B): RT 3.10 minutes; 197 (M−H)−.

Workup

  1. temperaturethen cooled
  2. customevaporated

Sources & evidence

ORD record
ord-23299135a5884d4386bb0b463a42a8fa
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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