Acetone → HCID 59253961, compound

HRID 638698Notes

Reaction equation

HRID 638698 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]([O-])([O-])=[O:14].[K+].[K+].[I-].[Na+].Cl[CH2:22][C:23]([O:25][CH3:26])=[O:24].C[C:28]([CH3:30])=[O:29]>>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[C:9]([O:12][CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:10]=[CH:11][C:2]=1[O:1][CH2:30][C:28]([O:14][CH3:13])=[O:29]

Participants

6

Reactant 5

HCID 180AcetoneHCID 5238Sodium IodideHCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 75077Methyl Gentisate

Product 1

HCID 59253961HCID 59253961, compoundYield 80%

Procedure

To a mixture of methyl 2,5-dihydroxybenzoate (34 g, 202 mmol), anhydrous K2CO3 (204 g, 1.476 mol) and sodium iodide (5 grams, 33.3 mmol) in anhydrous acetone (1000 ml) was added methyl chloroacetate (60.7 grams, 559 mmol) and refluxed for 20 hours. Acetone was distilled off and water (1500 ml) was added. Crude 4 was filtered, dried and recrystallised from toluene to give pure 4 (50.5 g, 80%) as a cream colored powder. The melting point was found to be 90-94° C. The structure was confirmed by NMR.

Workup

  1. temperaturerefluxed for 20 hours
  2. distillationAcetone was distilled off
  3. additionwater (1500 ml) was added
  4. filtrationCrude 4 was filtered
  5. customdried
  6. customrecrystallised from toluene

Sources & evidence

ORD record
ord-731ddb434fd94ebcb59cc1929d574cad
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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