Acetic Acid → HCID 13923414, compound

HRID 1253106Notes

Reaction equation

HRID 1253106 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]2[O:17][CH2:16][O:15][C:14]=12)[C:8]([O:10]C)=O.[C:18]([O:21][CH3:22])(=[O:20])[CH3:19].C(O)(=O)C>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]2[O:17][CH2:16][O:15][C:14]=12)[C:8]([CH2:19][C:18]([O:21][CH3:22])=[O:20])=[O:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6584Methyl AcetateHCID 24758Sodium hydrideHCID 601780Methyl 3,4-methylenedioxy-5-methoxybenzoate

Product 1

HCID 13923414HCID 13923414, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2.08 g (52 mmol) of 60% NaH was suspended in 8 ml of N,N-dimethylformamide (DMF) containing 4.20 g (20 mmol) of methyl 3-methoxy-4,5-methylenedioxybenzoate (9), and to this mixture was added dropwise with stirring 2.8 ml (35 mmol) of methyl acetate in 3 ml of dimethylformamide at such a rate that the temperature of the reaction mixture could be maintained at 50°-60° C. After this addition was over, the reaction mixture was kept at 55° C. for one hour, then cooled to room temperature and added with 3.8 ml of acetic acid to stop the reaction. The reaction mixture was added with 30 ml of ice-cold water and extracted with toluene (15 ml×2). The toluene layer was washed with water, further washed with a saturated sodium hydrogencarbonate aqueous solution, then dried over anhydrous magnesium sulfate and concentrated. The residue was washed several times with a small quantity of n-hexane and recrystallized from methanol (10 ml) to obtain 3.61 g of methyl 3-methoxy-4,5-methylenedioxybenzoylacetate (10) (yield: 71.6%). Melting point: 65.5°-66.5° C.

Workup

  1. additionto this mixture was added dropwise
  2. temperaturecould be maintained at 50°-60° C
  3. additionAfter this addition
  4. customthe reaction
  5. extractionextracted with toluene (15 ml×2)
  6. washThe toluene layer was washed with water
  7. washfurther washed with a saturated sodium hydrogencarbonate aqueous solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. washThe residue was washed several times with a small quantity of n-hexane
  11. customrecrystallized from methanol (10 ml)

Sources & evidence

ORD record
ord-9c405e205ccc44ea92f7998c7636095c
Source dataset
uspto-grants-1988_05
Patent number
US04746747

Reaction notes

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