Methanol → Methyl 4-hydroxy-alpha-methylcinnamate

HRID 359072Notes

Reaction equation

HRID 359072 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[C:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:19]O>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[C:7]([CH3:11])[C:8]([O:10][CH3:19])=[O:9])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2191964-Hydroxy-alpha-methylcinnamic acid

Product 1

HCID 53733305Methyl 4-hydroxy-alpha-methylcinnamate

Procedure

To 4-hydroxy-α-methylcinnamic acid (55 g), absolute methanol (400 ml) and conc. sulfuric acid (10 ml) were added and refluxed for 12 hours. After the reaction mixture was allowed to cool, it was concentrated under reduced pressure. To the residue was added water (300 ml), and the mixture was neutralized with sodium hydrogen carbonate, and the resulting precipitate was collected by filtration, washed with water, and recrystallized from ethyl acetate/nhexane to give methyl 4-hydroxy-α-methylcinnamate (53 g). mp. 103°-104° C.

Workup

  1. temperaturerefluxed for 12 hours
  2. temperatureto cool
  3. concentrationit was concentrated under reduced pressure
  4. additionTo the residue was added water (300 ml)
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customrecrystallized from ethyl acetate/nhexane

Sources & evidence

ORD record
ord-b9d74f490a764682b1881f9f54bec367
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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