2-Chloroethanol → 3-(2-Chloroethoxy)-2-ethyl-acrylic acid ethyl ester

HRID 1277740Notes

Reaction equation

HRID 1277740 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH:5]([CH:8]=[O:9])[CH2:6][CH3:7])[CH3:2].[Cl:11][CH2:12][CH2:13]O>C1C=CC=CC=1.S(=O)(=O)(O)[O-].[Na+]>[CH2:1]([O:3][C:4](=[O:10])[C:5]([CH2:6][CH3:7])=[CH:8][O:9][CH2:13][CH2:12][Cl:11])[CH3:2]

Participants

5

Reactant 2

HCID 342-ChloroethanolHCID 289299Ethyl 2-formylbutanoate2×

Product 1

HCID 538637943-(2-Chloroethoxy)-2-ethyl-acrylic acid ethyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 516919Sodium BisulfateCatalystHCID 241BenzeneSolvent

Procedure

28.8 g 2-Formyl-butyric acid ethyl ester was refluxed in 250 ml benzene with 54 g 2-chloroethanol in the presence of 250 mg sodium bisulfate, and the water of reaction formed thereby was withdrawn continuously. Conditions analogous to those in Example 1 were maintained to produce 34.5 g 3-(2-chloroethoxy)-2-ethyl-acrylic acid ethyl ester (84% yield) boiling at 104°-107° C./2 torr. nD23 =1.4719. The compound was hydrogenated as in Example 1, and 3-(2-chloroethoxy)-2-ethylpropionic acid ethyl ester was obtained in a yield of 81.5%. It boiled at 120°-122° C./14 torr, nD27 =1.4352.

Workup

  1. customformed
  2. customthereby was withdrawn continuously
  3. temperatureto those in Example 1 were maintained

Sources & evidence

ORD record
ord-f77f2e10cfc342b0abf41bab17012140
Source dataset
uspto-grants-1981_07
Patent number
US04278808

Reaction notes

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