Methanol → Methyl Ferulate

HRID 1678576Notes

Reaction equation

HRID 1678576 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[O:13][CH3:14].S(=O)(=O)(O)O.O.[CH3:21]O>>[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:21])=[O:11])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 445858Ferulic Acid

Product 1

HCID 5357283Methyl FerulateYield 97%

Procedure

To a solution of (E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid (3.0 g, 15 mmol) in methanol (30 mL) was added sulfuric acid (0.5 mL), and the mixture was heated under reflux for 12 hours. After the reaction solution was returned to room temperature, water was added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was washed with water, and then concentrated under reduced pressure to give the title compound (3.1 g, yield 97%) as an oily matter. The obtained compound was used in the next reaction without purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. customwas returned to room temperature
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-999be62c3fb64c1f93e0ca02f4d0f029
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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