Diethyl phenylmalonate → Diethyl 2-cyclohexylmalonate

HRID 2108182Notes

Reaction equation

HRID 2108182 reaction equation
[C:1]1([CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Rh]>[CH:1]1([CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 66514Diethyl phenylmalonate

Product 1

HCID 240541Diethyl 2-cyclohexylmalonate

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 5% rhodium on carbon (4.5 g) and diethyl phenylmalonate (30 g) in ethanol (100 ml) was hydrogenated at 60 psi for 18 hours. The suspension was filtered through celite and concentrated to a syrup (quant. yield). Distillation at 90°-94° C. (0.5 mmHg) afforded 28.2 g (92%) of the diethyl cyclohexylmalonate.

Workup

  1. filtrationThe suspension was filtered through celite

Sources & evidence

ORD record
ord-14dd2840bad0418aa294601f9286977a
Source dataset
uspto-grants-1990_06
Patent number
US04937355

Reaction notes

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