Hydrochloric Acid → 2-(4-Methylbenzyl)phenol

HRID 554539Notes

Reaction equation

HRID 554539 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)O)C1C=CC=CC=1.Cl>CO.[OH-].[Pd+2].[OH-]>[CH3:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 49963343(2-Benzyloxyphenyl)-p-tolylmethanol

Product 1

HCID 36460202-(4-Methylbenzyl)phenolYield 70.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2-benzyloxyphenyl)-p-tolylmethanol (1.5 g, 4.43 mmol) in methanol (27 mL), a 20% palladium hydroxide catalyst (150 mg) was added and furthermore 2N—HCl (0.37 mL) was added thereto. The 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 (1:10)] to obtain the title compound (617 mg, 70%).

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 (1:10)]

Sources & evidence

ORD record
ord-642da0582c4f444daa4f376acad3126d
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

Loading…