3-(2-Chloroethoxy)-2-ethylacrylic acid methyl ester → 3-(2-Chloroethoxy)-2-ethylpropionic acid methyl ester

HRID 1277738Notes

Reaction equation

HRID 1277738 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]([CH2:10][CH3:11])=[CH:5][O:6][CH2:7][CH2:8][Cl:9].[H][H]>C(O)C.[Ni]>[CH3:1][O:2][C:3](=[O:12])[CH:4]([CH2:10][CH3:11])[CH2:5][O:6][CH2:7][CH2:8][Cl:9]

Participants

5

Reactant 2

HCID 537981423-(2-Chloroethoxy)-2-ethylacrylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 542326673-(2-Chloroethoxy)-2-ethylpropionic acid methyl esterYield 82%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

37 g of 3-(2-Chloroethoxy)-2-ethylacrylic acid methyl ester (0.192 mole) was dispersed in 350 ml ethanol together with 6 g Raney nickel catalyst. The mixture was hydrogenated in a pressure vessel at 55°-60° C. at a hydrogen gage pressure of 30-60 atmospheres. When no further hydrogen was absorbed, the contents of the vessel were filtered to remove the catalyst, the solvent was distilled off, and the residue was fractionated in a vacuum. 3-(2-Chloroethoxy)-2-ethylpropionic acid methyl ester was obtained in an amount of 30.7 g (33.7 g) as a fraction boiling at 110° C. and 14 torr (82%-90% yield). nD20 =1.4399, d420 =1.083.

Workup

  1. customWhen no further hydrogen was absorbed
  2. filtrationthe contents of the vessel were filtered
  3. customto remove the catalyst
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-15ce32798c2c41de8734cd852485518a
Source dataset
uspto-grants-1981_07
Patent number
US04278808

Reaction notes

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