Water → 2-[4'-(4"-Chlorophenoxy)phenoxy]-propionic acid 4-chlorobut-1-yl ester

HRID 903380Notes

Reaction equation

HRID 903380 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:18]=[CH:17][C:10]([O:11][CH:12]([CH3:16])[C:13]([OH:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25]O.S(=O)(=O)(O)O.O>C(Cl)(Cl)Cl>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][O:14][C:13](=[O:15])[CH:12]([O:11][C:10]1[CH:17]=[CH:18][C:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][CH:19]=2)=[CH:8][CH:9]=1)[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 135694-Chloro-1-butanolHCID 64928Clofop

Product 1

HCID 544272872-[4'-(4"-Chlorophenoxy)phenoxy]-propionic acid 4-chlorobut-1-yl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

24.4 g=0.08 mol of 2-[4'-(4"-chlorophenoxy)phenoxy]-propionic acid, 10.8 g=0.1 mol of 4-chlorobutanol and 2 ml concentrated sulfuric acid in 50 ml chloroform were refluxed for 6 hours with azeotropic distillation of the reaction water. After cooling, the reaction mixture was washed twice with 100 ml water, neutralized with bicarbonate solution and washed with water until it was free from salt. After drying over calcium chloride and distillation of the solvent, 27.0 g=88% of the theory of 2-[4'-(4"-chlorophenoxy)phenoxy]-propionic acid 4-chlorobut-1-yl ester were obtained having a refractive index nD24 of 1.5517. ##STR16##

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed twice with 100 ml water
  3. washwashed with water until it
  4. dry with materialAfter drying over calcium chloride and distillation of the solvent, 27.0 g=88% of the theory of 2-[4'-(4"-chlorophenoxy)phenoxy]-propionic acid 4-chlorobut-1-yl ester
  5. customwere obtained

Sources & evidence

ORD record
ord-9eea7b03f4744be98d8b812d6cfd0338
Source dataset
uspto-grants-1980_10
Patent number
US04227009

Reaction notes

Loading…