تفاعل #1566917

معادلة التفاعل

methyl 4-(1-hydroxyethyl)benzoate

2-methylpropan-1-ol

bismuth(III) bromide

→

methyl 4-(1-isobutoxyethyl)benzoate

المردود 76.2%

المذيبات

perchloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 12 hours
2. 2
   تركيزThe suspension was concentrated in vacuum
3. 3
   أخرىquenched with aqueous 1N hydrochloric acid (5 mL)
4. 4
   استخلاصextracted with dichloromethane (50 mL)
5. 5
   استخلاصThe combined extract
6. 6
   تجفيفwas dried over sodium sulphate
7. 7
   أخرىevaporated
8. 8
   أخرىpurified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1)

الإجراء التجريبي

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).

المصدر