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

HRID 2308977Notes

Reaction equation

HRID 2308977 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-8bbefc96b9c34d849d2a0f4fb7e50a4e
Source dataset
uspto-grants-1987_09
Patent number
US04692446

Reaction notes

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