Hydrochloric Acid → HCID 22054265, compound

HRID 1830218Notes

Reaction equation

HRID 1830218 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:25])=[C:5]([C:16]([O:23][CH3:24])=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:15])=[C:11]([CH:14]=1)[CH:12]=[O:13].[OH-].[Na+].S(OC)(O[CH3:32])(=O)=O.Cl>C(O)C>[CH3:1][O:2][C:3]1[C:4]([CH3:25])=[C:5]([C:16]([O:23][CH3:24])=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:15][CH3:32])=[C:11]([CH:14]=1)[CH:12]=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 21919177HCID 21919177, compound

Product 1

HCID 22054265HCID 22054265, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-hydroxybenzaldehyde (0.500 g, 1.45 mmol) was dissolved in ethanol (15 ml) and after adding thereto in sequence sodium hydroxide (0.064 g, 1.59 mmol) and dimethyl sulfate (0.200 g, 1.59 mmol), the solution was stirred at room temperature for 12 hours. After the completion of reaction, the reaction solution was poured into a cold diluted hydrochloric acid solution and extracted with ethyl acetate. The extract was washed with water and then dried, the solvent was removed by distillation and the obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=4:1) to obtain the titled compound (0.359 g, 0.998 mmol, 69%).

Workup

  1. additionafter adding
  2. customAfter the completion of reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was removed by distillation
  7. customthe obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-ee78575fdbc6429abc1b784f0de733d9
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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