Methanol → HCID 23023480, compound

HRID 2222451Notes

Reaction equation

HRID 2222451 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][C:6]1([C:11]([O-:13])=[O:12])[CH2:10][CH2:9][CH2:8][O:7]1.S(=O)(=O)(O)O.[CH3:22]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][C:6]1([C:11]([O:13][CH3:22])=[O:12])[CH2:10][CH2:9][CH2:8][O:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 23023467HCID 23023467, compound

Product 1

HCID 23023480HCID 23023480, compound

Procedure

To a solution of 2.20 g of 2-(3-hydroxybenzyl)-tetrahydro-2-furancarboxylate in 50 ml of methanol was added 0.5 ml of sulfuric acid, and the mixture was heated under reflux for 18 hours. The solvent was evaporated, and the residue was dissolved in 200 ml of ethyl acetate. The organic layer washed twice with 50 ml of water, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography, to give 2.20 g of the title compound from the 7:3 hexane-ethyl acetate fraction.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in 200 ml of ethyl acetate
  5. washThe organic layer washed twice with 50 ml of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-74e19a126e904160bd2f0accb95c879d
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

Loading…