p-Toluenesulfonic acid → Methyl Caffeate

HRID 416031

Reaction equation

HRID 416031 reaction equation
[C:1]([OH:13])(=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1.[CH3:14]C1C=CC(S(O)(=O)=O)=CC=1.COC(OC)(C)C>CO>[C:1]([O:13][CH3:14])(=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 689043Caffeic Acid

Product 1

HCID 689075Methyl CaffeateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Put a 10 g caffeic acid (1) in a reaction bottle, and add 1 g TsOH and 3 ml 2,2-dimethoxypropane and 10 ml methanol thereinto, followed by refluxing for 6 hours. After the refluxation, remove the solvent and pour the resultant solution into 100 ml water, followed by being extracted by the ethyl acetate for three times, neutralizing with 3% NaHCO3, and finally performing a column chromatography. Therefore, the product, methyl caffeate (the compound 2) is obtained with 98% yield.

Workup

  1. temperatureby refluxing for 6 hours
  2. customAfter the refluxation, remove the solvent
  3. additionpour the resultant solution into 100 ml water
  4. extractionby being extracted by the ethyl acetate for three times

Sources & evidence

ORD record
ord-8061bc708c5948a997c7e01eb3eddcbe
Source dataset
uspto-grants-2012_01
Patent number
US08088818B2

Linked notes

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