Hydrochloric Acid → 2-(4-Isopropylbenzyl)phenol

HRID 554499Notes

Reaction equation

HRID 554499 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]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=1)O)C1C=CC=CC=1.Cl>CO.[OH-].[Pd+2].[OH-]>[CH:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])=[CH:18][CH:19]=1)([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67459620(2-Benzyloxyphenyl)-(4-isopropylphenyl)methanol

Product 1

HCID 133048432-(4-Isopropylbenzyl)phenolYield 73.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2-benzyloxyphenyl)-(4-isopropylphenyl)methanol (2.63 g, 7.92 mmol) in methanol (50 mL), a 20% palladium hydroxide catalyst (263 mg) was added and furthermore 2N—HCl (0.4 mL) was added thereto, and the mixture solution was stirred under a hydrogen atmosphere for 15 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, 73%).

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-3c910f4967294b45afb0f207f77df69b
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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