4-Chlorophenol → 4-Chloro-2-(4-ethylbenzyl)phenol

HRID 1297539Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15]O)=[CH:13][CH:12]=1)[CH3:10].CS(O)(=O)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:15][C:14]2[CH:17]=[CH:18][C:11]([CH2:9][CH3:10])=[CH:12][CH:13]=2)[CH:3]=1

Participants

Reactant 3

HCID 46844-Chlorophenol

HCID 6395Methanesulfonic Acid

HCID 130344-Ethylbenzyl alcohol

Product 1

HCID 230727454-Chloro-2-(4-ethylbenzyl)phenolYield 46.2%

Conditions

Temperature: 160 °C

Procedure

A mixture of 4-chlorophenol (2.0 g, 15.6 mmol), 4-ethylbenzylalcohol (2.12 g, 15.6 mmol) and methanesulfonic acid (80 mg, 0.83 mmol) was heated and stirred at 160° C. for 25 minutes. The reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 4-chloro-2-(4-ethylbenzyl)phenol (1.78 g, 46%) as a light-yellow oil.

Workup

temperaturewas heated
customThe reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record: ord-ecec4ac92e5440c9b5902ed5012dc3c6
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250522B2

Reaction notes

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