Isopropanol → Methyl4-(1-isopropoxyethyl)benzoate

HRID 1479729

Reaction equation

HRID 1479729 reaction equation
[CH3:1][CH:2](O)[CH3:3].[Bi](Br)(Br)Br.[OH:9][CH:10]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1)[CH3:11]>ClC(Cl)(Cl)Cl>[CH3:19][O:18][C:16](=[O:17])[C:15]1[CH:20]=[CH:21][C:12]([CH:10]([O:9][CH:2]([CH3:3])[CH3:1])[CH3:11])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 82232bismuth(III) bromideHCID 586417Methyl 4-(1-hydroxyethyl)benzoate

Product 1

HCID 89581255Methyl4-(1-isopropoxyethyl)benzoateYield 43.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To the solution of propan-2-ol (100 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, then methyl 4-(1-hydroxyethyl)benzoate (300 mg, 1.67 mmol) was added to the solution, the mixture was stirred at room temperature for 12 hours. Then the mixture was concentrated and Then the mixture was concentrated and purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1) to give methyl4-(1-isopropoxyethyl)benzoate (161 mg, 43%) as oil. 1H-NMR (300 MHz, CD3OD) δ 7.96 (d, J=8.4 Hz, 2H), 7.41 (d, J=8.4 Hz, 2H), 4.68-4.61 (m, 1H), 3.54-3.46 (m, 1H), 1.38 (d, 3H), 1.15 (d, 3H), 1.06 (d, 3H),

Workup

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

Sources & evidence

ORD record
ord-4905fe10b9784247bd71826f5995a8d8
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Linked notes

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