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Hydrochloric Acid → 4-(2,3,4,5-tetramethoxy-6-methylbenzyl)benzoic Acid

HRID 496353
Notes
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Reaction equation

HRID 496353 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:23])[C:5]([CH3:22])=[C:6]([CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[C:7](=O)[C:8]=1[O:9][CH3:10].[C:24](=O)([O-])[O-].[K+].[K+].Cl.[CH3:31][OH:32]>O>[CH3:31][O:32][C:7]1[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[C:4]([O:23][CH3:24])=[C:5]([CH3:22])[C:6]=1[CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 99488164-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)benzoic acid

Product 1

HCID 223252774-(2,3,4,5-tetramethoxy-6-methylbenzyl)benzoic AcidYield 76%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
70 °C

Procedure

The compound (160 mg, 0.45 mmol) obtained in Step 3 was dissolved in a mixture of an aqueous solution of potassium carbonate (91 mg, 0.66 mmol) in water (1 ml) and methanol (2 ml) and the mixture was stirred at 70° C. for 3 hours. The reaction mixture was acidified by adding concentrated hydrochloric acid and then was extracted with diethylether. The extract was washed with water, dried, and then the solvent was distilled off to yield the title compound (116 mg, 0.34 mmol, yield 76%).

Workup

  1. extractionwas extracted with diethylether
  2. washThe extract was washed with water
  3. customdried
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-4366638753ae478e9d958dd2bfa05daa
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06943196B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes