Hydrochloric Acid → HCID 22054254, compound

HRID 1830242Notes

Reaction equation

HRID 1830242 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:33])=[C:5]([C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:11]([CH:16]=1)[C:12]([O:14]C)=[O:13].Cl>[OH-].[Na+].O1CCOCC1.O>[CH3:1][O:2][C:3]1[C:4]([CH3:33])=[C:5]([C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:11]([CH:16]=1)[C:12]([OH:14])=[O:13]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 22054220HCID 22054220, compound

Product 1

HCID 22054254HCID 22054254, compoundYield 98.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-phenoxybenzoate (0.220 g, 0.487 mmol) was dissolved in a mixed solution of an aqueous 1N NaOH solution (3 ml) and 1,4-dioxane (5 ml) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was diluted with water, rendered acidic with concentrated hydrochloric acid and then extracted with ether. The extract was washed with water and then dried, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain the titled compound (0.210 g, 0.479 mmol, 98%).

Workup

  1. extractionextracted with ether
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-0f1a3f99469948ca9dda021da711d8b6
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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