3-Chloro-4-hydroxybenzaldehyde → Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-methylacrylate

HRID 1876367Notes

Reaction equation

HRID 1876367 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

4

Reactant 2

HCID 170223-Chloro-4-hydroxybenzaldehydeHCID 79792Ethyl 2-(triphenylphosphoranylidene)propionate

Product 1

HCID 67406957Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-methylacrylateYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 3-chloro-4-hydroxybenzaldehyde (0.783 g, 5 mmol) and ethyl 2-(triphenylphosphoranylidene)propionate (2.72 g, 7.5 mmol) in anhydrous tetrahydrofuran (25 mL) was heated at 60° C. under nitrogen for 4 hours. The solvent was removed in vacuo and purified by silica gel chromatography (40% EtOAc in hexanes) to provide ethyl 3-(3-chloro-4-hydroxyphenyl)-2-methylacrylate (515) (1.11 g, 95.2%) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. custompurified by silica gel chromatography (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-186de98249b244b0a150ba14ed09c4a8
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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