Acetone → HCID 59253961, compound

HRID 2169691Notes

Reaction equation

HRID 2169691 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-42920ceab64f4bac8aabef75435d5fda
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

Loading…