Water → 2-[p-(2,4-Dichlorobenzyl)-phenoxi]-butyric acid ethyl ester

HRID 371891

Reaction equation

HRID 371891 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[CH2:17]([O:19][C:20](=[O:25])[CH:21](Cl)[CH2:22][CH3:23])[CH3:18].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:17]([O:19][C:20](=[O:25])[CH:21]([O:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C:3]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:2]=2[Cl:1])=[CH:10][CH:9]=1)[CH2:22][CH3:23])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 123252Ethyl 2-chlorobutanoateHCID 139387094-(2,4-Dichlorobenzyl)-phenol

Product 1

HCID 706231782-[p-(2,4-Dichlorobenzyl)-phenoxi]-butyric acid ethyl esterYield 45.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 25.3 g of 4-(2,4-dichlorobenzyl)-phenol and 15 g of α-chlorobutyric acid ethyl ester in 100 ml of dimethyl formamide were stirred for 2 hours at 100° C with 16 g of potassium carbonate. After cooling, the reaction mixture was poured into 1 liter of water. An oil precipitated which was separated and dried over sodium sulfate. By vacuum distillation, 16.8 g of 2-[p-(2,4-dichlorobenzyl)-phenoxi]-butyric acid ethyl ester were obtained. b.p. 180° - 183° C/0.8 mm Hg/nD21 : 1.5912 ##STR7## The following compounds were prepared according to the methods described in the above Examples.

Workup

  1. temperatureAfter cooling
  2. customAn oil precipitated which
  3. customwas separated
  4. dry with materialdried over sodium sulfate
  5. distillationBy vacuum distillation

Sources & evidence

ORD record
ord-90f266f1bf5e4a3fb18e4471427ba76a
Source dataset
uspto-grants-1978_05
Patent number
US04088474

Linked notes

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