Water → Propionic acid, 2-(4-(4-chlorobenzyl)phenoxy)-, ethyl ester, (+-)-

HRID 371889Notes

Reaction equation

HRID 371889 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:16]([O:18][C:19](=[O:23])[CH:20](Br)[CH3:21])[CH3:17].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:16]([O:18][C:19](=[O:23])[CH:20]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:15][CH:14]=2)=[CH:8][CH:9]=1)[CH3:21])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 131220024-[(4-Chlorophenyl)methyl]phenol

Product 1

HCID 3054670Propionic acid, 2-(4-(4-chlorobenzyl)phenoxy)-, ethyl ester, (+-)-Yield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 22 g of 4-(4-chlorobenzyl)-phenol and 18.5 g of α-bromopropionic acid ethyl ester in 100 ml of dimethyl formamide was stirred for 2 hours at 100° C together 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 means of vacuum distillation, 23.3 g of 2-[p-(4-chlorobenzyl)-phenoxi]-propionic acid ethyl ester were obtained. b.p.: 146° - 151° C/0.1 mm Hg/nD22 : 1.5527 ##STR4##

Workup

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

Sources & evidence

ORD record
ord-de1f2cffc29a446bb28c94d8070859aa
Source dataset
uspto-grants-1978_05
Patent number
US04088474

Reaction notes

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