2-Chloroethanol → 2-[4'-(2",4"-Dichlorophenoxy)-phenoxy]-propionic acid 2-chloroeth-1-yl ester

HRID 903379Notes

Reaction equation

HRID 903379 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH:10]([CH3:14])[C:11](Cl)=[O:12])=[CH:7][CH:6]=1.C(O)(=O)CC.S(Cl)(Cl)=O.[CH2:31]([Cl:34])[CH2:32][OH:33]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[Cl:34][CH2:31][CH2:32][O:33][C:11](=[O:12])[CH:10]([O:9][C:8]1[CH:15]=[CH:16][C:5]([O:4][C:3]2[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:2]=2[Cl:1])=[CH:6][CH:7]=1)[CH3:14]

Participants

7

Reactant 4

HCID 342-ChloroethanolHCID 1032Propionic AcidHCID 24386Thionyl ChlorideHCID 129429952-[4-(2,4-Dichlorophenoxy)phenoxy]propanoyl chloride

Product 1

HCID 545418052-[4'-(2",4"-Dichlorophenoxy)-phenoxy]-propionic acid 2-chloroeth-1-yl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 0.06 mol=20.73 g of 2-[4'-(2",4"-dichlorophenoxy)phenoxy]-propionic acid chloride, prepared from 2-[4'-2",4"-dichlorophenoxy)phenoxy]-propionic acid and thionyl chloride, in 60 ml absolute toluene was added dropwise at room temperature to a solution of 0.06 mol=4.83 g of ethylene chlorohydrin (2-chloroethanol) and 0.06 mol=6.06 g of triethylamine in 60 ml absolute toluene. After the addition, stirring of the mixture was continued for 1 hour at 50° C., the precipitated triethylamine chloride was filtered off, and the filtrate was washed with dilute sodium hydroxide solution and with water. The toluene solution was dried over sodium sulfate and the solvent was distilled off under reduced pressure. 21.25 g=91% of the theory of 2-[4'-(2",4"-dichlorophenoxy)-phenoxy]-propionic acid 2-chloroeth-1-yl ester were obtained having a refractive index nD24 of 1.5672. ##STR13##

Workup

  1. additionAfter the addition
  2. filtrationthe precipitated triethylamine chloride was filtered off
  3. washthe filtrate was washed with dilute sodium hydroxide solution and with water
  4. dry with materialThe toluene solution was dried over sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1385d9537f6846bdb3550df61e6ae484
Source dataset
uspto-grants-1980_10
Patent number
US04227009

Reaction notes

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