1-Pyrrolidineethanol → 2-[4'-(2",4"-Dichloro-phenoxy)phenoxy]-propionic acid 2-pyrrolidino-eth-1-yl ester hydrochloride

HRID 903381Notes

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.[N:22]1([CH2:27][CH2:28][OH:29])[CH2:26][CH2:25][CH2:24][CH2:23]1>C1(C)C=CC=CC=1>[ClH:1].[N:22]1([CH2:27][CH2:28][O:29][C:11](=[O:12])[CH:10]([O:9][C:8]2[CH:15]=[CH:16][C:5]([O:4][C:3]3[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:2]=3[Cl:1])=[CH:6][CH:7]=2)[CH3:14])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

Conditions

Temperature: 60 °C

Procedure

0.06 mol=20.73 g of 2-[4'-(2",4"-dichlorophenoxy)phenoxy]-propionic acid chloride dissolved in 30 ml absolute toluene were added dropwise at room temperature to a solution of 0.06 mol=6.9 g of 2-pyrrolidino-ethanol in 50 ml absolute toluene and the mixture was stirred for a further hour at 60° C. After cooling to 0° C., the formed precipitate was filtered off and recrystallized from acetone. 21.0 g=76% of the theory of 2-[4'-(2",4"-dichloro-phenoxy)phenoxy]-propionic acid 2-pyrrolidino-eth-1-yl ester hydrochloride were obtained melting at 160°-162° C. ##STR17##

Workup

temperatureAfter cooling to 0° C.
filtrationthe formed precipitate was filtered off
customrecrystallized from acetone

Sources & evidence

ORD record: ord-f1f69a86a6204a6fbb528c442270d1d5
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04227009

Reaction notes

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