Water → 3-Oxo-hexanoic acid-1-(3,3-dimethyl-cyclohexyl)-ethyl ester

HRID 1751173Notes

Reaction equation

HRID 1751173 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH2:6][CH2:5][CH:4]([CH:8]([OH:10])[CH3:9])[CH2:3]1.C(O[C:15]([CH2:17][CH2:18][C:19](=[O:23])[CH2:20][CH2:21]C)=O)C.CC[O-:26].[Na+].O>C(O)C.C1(C)C=CC=CC=1>[CH3:11][C:2]1([CH3:1])[CH2:7][CH2:6][CH2:5][CH:4]([CH:8]([O:10][C:21](=[O:26])[CH2:20][C:19](=[O:23])[CH2:18][CH2:17][CH3:15])[CH3:9])[CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 91338Cyclohexanemethanol, alpha,3,3-trimethyl-HCID 2723922Sodium ethoxideHCID 12271529Ethyl 4-oxoheptanoate

Product 1

HCID 675167043-Oxo-hexanoic acid-1-(3,3-dimethyl-cyclohexyl)-ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

78 g (0.5 mol) of 1-(3,3-dimethyl-cyclohexyl)-ethanol, 86.9 g (0.55 mol) of 3-oxo-hexanecarboxylic acid ethyl ester and 0.6 g sodium ethylate in 50 g ethanol were placed in a 500-ml stirred vessel and boiled under reflux, distilling-off the ethanol via a still head. Then 100 ml water and 100 ml toluene were added to the reaction solution at room temperature, the aqueous phase was separated, the organic phase was washed with water until neutral and concentrated by evaporation. The raw product (139 g) was fractionated on a 30-cm Vigreux column in vacuum.

Workup

  1. customthe aqueous phase was separated
  2. washthe organic phase was washed with water until neutral and
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-7b5c2e79de0c47b8ba2d40445083f433
Source dataset
uspto-grants-2015_10
Patent number
US09157048B2

Reaction notes

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