Acetic Acid → HCID 12243185, compound

HRID 1637512Notes

Reaction equation

HRID 1637512 reaction equation
C([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([O:16][CH3:17])[CH:7]=1)(=O)C.C[O-].[Na+].C(O)(=O)C>CO>[OH:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([O:16][CH3:17])[CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 19348440HCID 19348440, compound

Product 1

HCID 12243185HCID 12243185, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The whole of the crude methyl 4-acetoxymethyl-2-methoxybenzoate thus obtained was dissolved in 100 ml of methanol, and 9.6 ml (4.9 mmol) of a 0.51 M sodium methoxide solution in methanol were added to the solution. The resulting mixture was then stirred for 1 hour. At the end of this time, 0.6 ml of acetic acid were added, to terminate the reaction, and then the reaction mixture was freed from the solvent by distillation under reduced pressure . The resulting residue was mixed with water, and the resulting aqueous solution was extracted with a mixture of ethyl acetate and hexane. The extract was washed with a saturated aqueous solution of sodium hydrogencarbonate, with water and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 250 g of silica gel, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 4.39 g of the title compound as an oily substance in a 53% yield (total yield of three steps).

Workup

  1. customto terminate
  2. customthe reaction
  3. distillationthe reaction mixture was freed from the solvent by distillation under reduced pressure
  4. additionThe resulting residue was mixed with water
  5. extractionthe resulting aqueous solution was extracted with a mixture of ethyl acetate and hexane
  6. washThe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate, with water and with a saturated aqueous solution of sodium chloride, in that order
  7. dry with materialafter which it was dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customthe resulting residue was purified by column chromatography through 250 g of silica gel
  10. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-6fbff173adea4f86a2b31a90c49d3982
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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