Cyclohexanol → HCID 89581398, compound

HRID 1501173Notes

Reaction equation

HRID 1501173 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Bi](Br)(Br)Br.O[CH:13]([C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)[CH3:14]>C(Cl)(Cl)(Cl)Cl>[CH:1]1([O:7][CH:13]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)[CH3:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 82232bismuth(III) bromideHCID 586417Methyl 4-(1-hydroxyethyl)benzoate

Product 1

HCID 89581398HCID 89581398, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To the solution of cyclohexanol (167 mg, 1.67 mmol) in carbon tetrachloride (50 mL) was added bismuth (III) bromide (744.4 mg, 1.67 mmol), the mixture was stirred for 30 minutes at room temperature, the methyl 4-(1-hydroxyethyl)benzoate (300 mg, 1.67 mmol) was added, the mixture was stirred at room temperature for 12 hours. Then the mixture was concentrated and purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1) to give methyl 4-(1-(cyclohexyloxy)ethyl)benzoate (60 mg, 14%) as oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. concentrationThen the mixture was concentrated
  3. custompurified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-fc84025f00f44753b0b0d3896d29067a
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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