Hydrochloric Acid → 2-(4-Methoxybenzyl)-4-methoxyphenol

HRID 554516

Reaction equation

HRID 554516 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[CH:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)O)C1C=CC=CC=1.Cl>CO.[OH-].[Pd+2].[OH-]>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:17][C:10]2[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:9]=2[OH:8])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67459059(2-Benzyloxy-5-methoxyphenyl)-(4-methoxyphenyl)methanol

Product 1

HCID 674612982-(4-Methoxybenzyl)-4-methoxyphenolYield 91.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2-benzyloxy-5-methoxyphenyl)-(4-methoxyphenyl)methanol (2.54 g, 7.25 mmol) in methanol (50 ml), a 20% palladium hydroxide catalyst (250 mg) was added and furthermore 36% HCl (0.25 mL) was added thereto. The mixture was stirred under a hydrogen atmosphere for 14 hours, and then the catalyst was filtered off. The solvent was distilled under reduced pressure, and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:4)] to obtain the title compound (1.62 g, 91%).

Workup

  1. filtrationthe catalyst was filtered off
  2. distillationThe solvent was distilled under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:4)]

Sources & evidence

ORD record
ord-e7663b6b75a740c5ab16acf93ee0385e
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Linked notes

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