4-Bromophenol → 4-Bromo-2-(1-methylcyclohexyl)phenol

HRID 249025Notes

Reaction equation

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

Participants

Reactant 2

HCID 78084-Bromophenol

HCID 14502Methylenecyclohexane

Product 1

HCID 105638754-Bromo-2-(1-methylcyclohexyl)phenolYield 19%

Conditions

Temperature: 80 °C

Procedure

A mixture of methylene cyclohexane (0.96 g, 10 mmoles), p-bromophenol (1.73 g, 10 mmoles) and acid resin (Dowex 50×12--150 mg) is heated at 80° C. for 16 hours. The residue is purified by silica gel chromatography (eluant: 50/50 mixture of CH2Cl2 /hexane). On evaporation of the solvents 0.50 g (19% yield) of 4-bromo-2-(1-methylcyclohexyl) phenol in the form of a yellowish oil is obtained.

Workup

customThe residue is purified by silica gel chromatography (eluant: 50/50 mixture of CH2Cl2 /hexane)

Sources & evidence

ORD record: ord-8eb7dbf5aedb4c2d84636f035cfb8daf
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05212203

Reaction notes

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