Methanol → Methyl 3-Coumarate

HRID 709745Notes

Reaction equation

HRID 709745 reaction equation
[OH:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.O.[CH3:19]O>>[OH:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:19])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 6375413-coumaric acid, (E)-

Product 1

HCID 5352910Methyl 3-Coumarate

Conditions

Temperature
70 °C

Procedure

To a solution of (E)-3-(3-hydroxyphenyl)acrylic acid (15.0 g) in methanol (100 mL) was added sulfuric acid (2.0 mL), and the mixture was stirred at 70° C. for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (15.8 g) as white crystals. This compound was used for the next step without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1b2b6add5687411eacafd694388b780f
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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