2,2,2-Trichloroethyl acrylate → 2-Chloro-3-[4-(3-hydroxy-propyl)-phenyl]-propionic acid 2,2,2-trichloro-ethyl ester

HRID 709449

Reaction equation

HRID 709449 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[Cl:12][C:13]([Cl:21])([Cl:20])[CH2:14][O:15][C:16](=[O:19])[CH:17]=[CH2:18].COC(=O)C([Cl:35])CC1C=CC(CO)=CC=1>>[Cl:12][C:13]([Cl:21])([Cl:20])[CH2:14][O:15][C:16](=[O:19])[CH:17]([Cl:35])[CH2:18][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1817502,2,2-Trichloroethyl acrylateHCID 2204244-AminobenzenepropanolHCID 866502982-Chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester

Product 1

HCID 866503002-Chloro-3-[4-(3-hydroxy-propyl)-phenyl]-propionic acid 2,2,2-trichloro-ethyl ester

Procedure

The title compound was prepared from 3-(4-amino phenyl)-propan-1-ol (1.02 g, 6.72 mmol) and acrylic acid 2,2,2-trichloroethylester (4.55 g, 22.17 mmol) in the same manner as described for 2-chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester. The crude product was purified by flash chromatography using DCM/iPrOH 95:5 as the eluent and the product was obtained as an oil (0.74 g, 29.4%). 1H NMR (300 MHz, CDCl3): δ 7.08-7.30 (m, 4H), 4.56-4.60 (t, 1H), 3.63-3.65 (m, 3H), 3.35-3.43 (dd, 1H), 3.18-3.25 (dd, 1H), 2.63-2.68 (m, 3H), 1.84-1.86 (m, 2H).

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-04c73670765046d8b96d7b31b51ea4d0
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Linked notes

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