Methanol → HCID 54516331, compound

HRID 235196Notes

Reaction equation

HRID 235196 reaction equation
[C:1]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:13][CH:12]=1)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:23]O>S(=O)(=O)(O)O>[C:1]([C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:16]=1)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 54217023HCID 54217023, compound

Product 1

HCID 54516331HCID 54516331, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 10.00 g of 4-(4-cinnamoylphenyl)butyric acid in 50 ml of methanol, 0.25 ml of sulfuric acid was added, and the mixture was refluxed for 1 hour. The solvent was removed under reduced pressure, and then the residue was added with water and extracted with ether. The ether layer was washed with water and dried, and then the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (methylene chloride:n-hexane=3:2) to yield 8.94 g of pale yellow crystals. Recrystallization from n-hexane gave pale yellow needles, mp 43°~44° C.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue was added with water
  4. extractionextracted with ether
  5. washThe ether layer was washed with water
  6. customdried
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (methylene chloride:n-hexane=3:2)

Sources & evidence

ORD record
ord-2af8d2195f874a12bba49832d7f7224c
Source dataset
uspto-grants-1997_01
Patent number
US05597848

Reaction notes

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