Isobutanol → HCID 89581006, compound

HRID 2170475Notes

Reaction equation

HRID 2170475 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][OH:4].[Bi](Br)(Br)Br.O[CH:11]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)[CH3:12]>ClC(Cl)(Cl)Cl>[CH2:3]([O:4][CH:11]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)[CH3:12])[CH:2]([CH3:5])[CH3:1]

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 82232bismuth(III) bromideHCID 586417Methyl 4-(1-hydroxyethyl)benzoate

Product 1

HCID 89581006HCID 89581006, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-methylpropan-1-ol (150 mg, 2 mmol) in perchloromethane (4 mL) was added bismuth(III) bromide (900 mg, 2 mmol). The mixture was stirred at room temperature for 30 minutes then methyl 4-(1-hydroxyethyl)benzoate (180 mg, 1 mmol) was added and the mixture was stirred at room temperature for 12 hours. The suspension was concentrated in vacuum and quenched with aqueous 1N hydrochloric acid (5 mL). The residue was taken up with water (50 mL) and extracted with dichloromethane (50 mL). The combined extract was dried over sodium sulphate, evaporated and purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1) to give the product methyl 4-(1-isobutoxyethyl)benzoate (0.18 g, 76%) as colorless oil. 1H NMR (300 MHz, CD3OD) δ 8.01 (d, J=8.1 Hz, 2H), 7.36 (d, J=8.1 Hz, 2H), 4.44-4.41 (m, 1H), 3.12-3.00 (m, 2H), 1.87-1.82 (m, 1H), 1.44 (d, J=6.3 Hz, 3H), 0.88 (d, J=6.6 Hz, 6H).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. concentrationThe suspension was concentrated in vacuum
  3. customquenched with aqueous 1N hydrochloric acid (5 mL)
  4. extractionextracted with dichloromethane (50 mL)
  5. extractionThe combined extract
  6. dry with materialwas dried over sodium sulphate
  7. customevaporated
  8. custompurified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-39288803b42c4e9e9f9749a18c093837
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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