Methanol → Methyl 4-(1-methoxyethyl)benzoate

HRID 1479726

Reaction equation

HRID 1479726 reaction equation
[CH3:1]O.[Bi](Br)(Br)Br.[OH:7][CH:8]([C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)[CH3:9]>ClC(Cl)(Cl)Cl>[CH3:17][O:16][C:14](=[O:15])[C:13]1[CH:18]=[CH:19][C:10]([CH:8]([O:7][CH3:1])[CH3:9])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 82232bismuth(III) bromideHCID 586417Methyl 4-(1-hydroxyethyl)benzoate

Product 1

HCID 14597192Methyl 4-(1-methoxyethyl)benzoateYield 57%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To the solution of methanol (53 mg, 1.67 mmol) in perchloromethane (80 mL) was added bismuth (III) bromide (743 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-methoxyethyl)benzoate (185 mg, 57%), 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-d2d43a9475f9494c8b9dcb738c8fe8bd
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Linked notes

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