Water → 4-Methoxy-3-oxo-butyric acid-1-(3,3-dimethylcyclohexyl)-ethyl ester

HRID 1751172Notes

Reaction equation

HRID 1751172 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.COC([CH2:16][CH2:17][C:18](=[O:22])[CH2:19][O:20][CH3:21])=O.CC[O-:25].[Na+].O>CO.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:16](=[O:25])[CH2:17][C:18](=[O:22])[CH2:19][O:20][CH3:21])[CH3:9])[CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 91338Cyclohexanemethanol, alpha,3,3-trimethyl-HCID 2723922Sodium ethoxideHCID 197524134-Methoxy-3-oxo-butanecarboxylic acid methyl ester

Product 1

HCID 675154674-Methoxy-3-oxo-butyric acid-1-(3,3-dimethylcyclohexyl)-ethyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Procedure

78 g (0.5 mol) of 1-(3,3-dimethyl-cyclohexyl)-ethanol, 80.3 g (0.55 mol) of 4-methoxy-3-oxo-butanecarboxylic acid methyl ester and 0.6 g sodium ethylate in 50 g methanol were placed in a 500-ml stirred vessel and boiled under reflux, distilling-off the methanol 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 (136 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-3daca685e8bf4f87a8aeebc577f0d2f7
Source dataset
uspto-grants-2015_10
Patent number
US09157048B2

Reaction notes

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