Water → Dimethyl (4-oxocyclohexyl)malonate

HRID 1530811Notes

Reaction equation

HRID 1530811 reaction equation
O.O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)O.O.[OH:20][CH:21]1[CH2:26][CH2:25][CH:24]([CH:27]([C:32]([O:34][CH3:35])=[O:33])[C:28]([O:30][CH3:31])=[O:29])[CH2:23][CH2:22]1>C(OCC)C>[O:20]=[C:21]1[CH2:26][CH2:25][CH:24]([CH:27]([C:28]([O:30][CH3:31])=[O:29])[C:32]([O:34][CH3:35])=[O:33])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 108005Sodium dichromate dihydrateHCID 91368111Dimethyl (4-hydroxycyclohexyl)malonate

Product 1

HCID 46238246Dimethyl (4-oxocyclohexyl)malonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At 5° C., a mixture of 22.7 g of sodium dichromate dihydrate, 17 ml of concentrated sulfuric acid and 113 ml of water was added dropwise to a solution of 47.7 g of dimethyl (4-hydroxycyclohexyl)malonate in 250 ml of diethyl ether. The mixture was stirred at room temperature for 4 hours, the organic phase was separated off and the aqueous phase was once more extracted with diethyl ether. The combined organic phases were dried and concentrated to give the title product as a yellow oil which was used without any further purification for the next step.

Workup

  1. customthe organic phase was separated off
  2. extractionthe aqueous phase was once more extracted with diethyl ether
  3. customThe combined organic phases were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-065faac959dd44099ade7a2c885b1532
Source dataset
uspto-grants-2001_03
Patent number
US06197729B1

Reaction notes

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