3-(2-Hydroxyethoxy)-2-ethyl-acrylic acid methyl ester → 3-(2-Hydroxyethoxy)-2-ethyl-propionic acid methyl ester

HRID 1277743Notes

Reaction equation

HRID 1277743 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]([CH2:10][CH3:11])=[CH:5][O:6][CH2:7][CH2:8][OH:9]>CO.[C].[Pd]>[CH3:1][O:2][C:3](=[O:12])[CH:4]([CH2:10][CH3:11])[CH2:5][O:6][CH2:7][CH2:8][OH:9]

Participants

4

Reactant 1

HCID 537667643-(2-Hydroxyethoxy)-2-ethyl-acrylic acid methyl ester

Product 1

HCID 543930243-(2-Hydroxyethoxy)-2-ethyl-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

28 g 3-(2-hydroxyethoxy)-2-ethyl-acrylic acid methyl ester was hydrogenated in 100 ml methanol in the presence of 2 g 5% palladium-carbon catalyst at atmospheric pressure. 24 g 3-(2-hydroxyethoxy)-2-ethyl-propionic acid methyl ester boiling at 104°-107° C./0.1 torr (84% yield) was recovered from the filtered hydrogenation mixture after evaporation of the solvent and vacuum distillation and identified by its carbon content of 54.35% (54.54% calculated for C8H16O4).

Workup

  1. custom24 g 3-(2-hydroxyethoxy)-2-ethyl-propionic acid methyl ester boiling at 104°-107° C./0.1 torr (84% yield) was recovered from the filtered hydrogenation mixture
  2. customafter evaporation of the solvent and vacuum distillation

Sources & evidence

ORD record
ord-eec13eaa5dc24cfc89cf742e89fd3953
Source dataset
uspto-grants-1981_07
Patent number
US04278808

Reaction notes

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