Hydrochloric Acid → 3-Methoxy-2-(4-methoxybenzyl)phenol

HRID 554545Notes

Reaction equation

HRID 554545 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15]C)[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-]>[CH3:1][O:8][C:9]1[C:10]([CH2:17][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67459057(2-Benzyloxy-6-methoxyphenyl)-(4-methoxyphenyl)methanol

Product 1

HCID 674596753-Methoxy-2-(4-methoxybenzyl)phenolYield 89%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2-benzyloxy-6-methoxyphenyl)-(4-methoxyphenyl)-methanol (2.13 g, 6.08 mmol) in methanol (50 mL), a 20% palladium hydroxide catalyst (0.32 g) was added and furthermore 2N—HCl (1.8 mL) was added thereto. The reaction mixture was stirred under a hydrogen atmosphere for 24 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 (1.31 g, 89%).

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-8b107e4717b54e468ca4bf98c8ce82c3
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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