Salicylaldehyde → Methyl 3-(2-hydroxyphenyl)prop-2-enoate

HRID 1533246Notes

Reaction equation

HRID 1533246 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][O:11][C:12]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13]>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:14][C:12]([O:11][CH3:10])=[O:13]

Participants

4

Reactant 2

HCID 6998SalicylaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 89400Methyl 3-(2-hydroxyphenyl)prop-2-enoateYield 69.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-hydroxybenzaldehyde (2.44 g) in toluene (25 ml) was added methoxycarbonylmethylene-triphenylphosphorane (6.68 g) and the mixture was stirred for 3 hours at ambient temperature. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography [eluting with ethyl acetate - n-hexane (1:1)] to give methyl 3-(2-hydroxyphenyl)acrylate (2.47 g).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography [eluting with ethyl acetate - n-hexane (1:1)]

Sources & evidence

ORD record
ord-29906bf82b79439bb8fbf05c6748fa59
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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