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

HRID 1164998Notes

Reaction equation

HRID 1164998 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].[CH3:13]O>S(=O)(=O)(O)O>[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([O:8][CH3:13])=[O:7]

Participants

4

Reactant 2

HCID 887MethanolHCID 119683-(2-Hydroxyphenyl)-2-propenoic acid

Product 1

HCID 89400Methyl 3-(2-hydroxyphenyl)prop-2-enoateYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of 200 g (1.218 mole) of 2-hydroxycinnamic acid in 2L of anhydrous methanol was treated with 10 drops of concentrated sulfuric acid. This solution was refluxed for 72 hr., using a Soxhlet extractor charged with 200 g of 3A molecular sieves. The methanolic solution was then concentrated under reduced pressure and cooled to afford 200 g (92%) of white crystals, which were used directly in the next step without additional purification.

Workup

  1. temperatureThis solution was refluxed for 72 hr
  2. concentrationThe methanolic solution was then concentrated under reduced pressure
  3. temperaturecooled

Sources & evidence

ORD record
ord-be57951fd8e942fcb9f559f8ba454413
Source dataset
uspto-grants-1990_03
Patent number
US04906661

Reaction notes

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