3-Butenoic acid → 3-Butenoic acid 2-(4-phenoxyphenoxy)-ethyl ester

HRID 1901437Notes

Reaction equation

HRID 1901437 reaction equation
[O:1]([C:8]1[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](O)(=[O:22])[CH2:19][CH:20]=[CH2:21]>ClCCl.N1(C2C=CN=CC=2)CCCC1>[O:1]([C:8]1[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH2:14][O:15][C:18](=[O:22])[CH2:19][CH:20]=[CH2:21])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 327433-Butenoic acidHCID 46767252-(4-Phenoxyphenoxy)ethanol

Product 1

HCID 541662683-Butenoic acid 2-(4-phenoxyphenoxy)-ethyl esterYield 89.5%

Reagents, catalysts & solvents 2

HCID 755674-PyrrolidinopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.05 g of 4-pyrrolidinopyridine and 17.25 g of 2-(4-phenoxyphenoxy)-ethanol are added at room temperature, with stirring, to a solution of 6.45 g of 3-butenoic acid in 100 ml of dichloromethane. At a temperature of 0° C., 17.0 g (82.5 mmol) of N,N-dicyclohexylcarbodiimide are then added in portions, and the reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is filtered. The precipitate which has been separated off is discarded, and the filtrate is washed with water and dried over sodium sulfate. After concentration by evaporation, the oily residue is purified by column chromatography on silica gel with hexane/ethyl acetate (9:1), yielding 20.0 g of 3-butenoic acid 2-(4-phenoxyphenoxy)-ethyl ester of the formula ##STR12## in the form of a colourless oil having a refractive index of nD23 : 1.5538.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customThe precipitate which has been separated off
  3. washthe filtrate is washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationAfter concentration
  6. customby evaporation
  7. customthe oily residue is purified by column chromatography on silica gel with hexane/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-1376f5abcff54a9db7fef69f06fb77dd
Source dataset
uspto-grants-1996_11
Patent number
US05578595

Reaction notes

Loading…