Ethanol → Methyl 4-(1-ethoxyethyl)benzoate

HRID 1479732

Reaction equation

HRID 1479732 reaction equation
[CH2:1]([OH:3])[CH3:2].[Bi](Br)(Br)Br.O[CH:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH3:10]>ClC(Cl)(Cl)Cl>[CH2:1]([O:3][CH:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH3:10])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 82232bismuth(III) bromideHCID 586417Methyl 4-(1-hydroxyethyl)benzoate

Product 1

HCID 89580551Methyl 4-(1-ethoxyethyl)benzoateYield 55%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To the solution of ethanol (77 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-ethoxy ethyl)benzoate (191 mg, 55%) 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-366d626554ab459fa8f19e26ecee9cea
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Linked notes

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