Water → HCID 67515461, compound

HRID 1751171Notes

Reaction equation

HRID 1751171 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:7][CH2:6][CH2:5][CH:4]([CH:8]([O:10][C:11](=[O:14])[CH2:12][OH:13])[CH3:9])[CH2:3]1.N1C=CC=C[CH:17]=1.C[O:23][CH2:24][C:25](Cl)=O.[OH2:28]>CC(OC)(C)C.C1(C)C=CC=CC=1>[CH3:15][C:2]1([CH3:1])[CH2:7][CH2:6][CH2:5][CH:4]([CH:8]([O:10][C:11](=[O:14])[CH2:12][O:13][CH3:17])[C:9]([O:23][CH2:24][CH3:25])=[O:28])[CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 22635021HCID 22635021, compound

Product 1

HCID 67515461HCID 67515461, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

53.5 g (0.25 mol) of hydroxyacetic acid-1-(3,3-dimethyl-cyclohexyl)-ethyl ester and 25.7 g (0.325 mol) of pyridine in 100 ml MTBE were placed in a 500-ml stirred vessel. Then 28.1 g (0.26 mol) of methoxyacetic acid chloride was added dropwise at room temperature, with cooling. 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 dilute sulfuric acid, soda solution and water until neutral and concentrated by evaporation. The raw product (73 g) was fractionated on a 30-cm Vigreux column in vacuum.

Workup

  1. temperaturewith cooling
  2. customthe aqueous phase was separated
  3. washthe organic phase was washed with dilute sulfuric acid, soda solution and water until neutral and
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0d4da6cf1fe94aaeb26bebf0ec63b562
Source dataset
uspto-grants-2015_10
Patent number
US09157048B2

Reaction notes

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