Реакция #43908

Уравнение реакции

2,3,5-trimethylphenol

Dichloromethyl methyl ether

ammonium chloride

→

title compound

Выход 40.1%

2-hydroxy-3,4,6-trimethylbenzaldehyde

Выход 40.1%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Температураcooled
2. 2
   workup.STIRRINGthe mixture was further stirred for 6 hr
3. 3
   Экстракцияextracted with dichloromethane
4. 4
   ПромывкаThe extract was washed successively with diluted hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated brine
5. 5
   Сушкаdried over anhydrous magnesium sulfate
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   ДругоеThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-50:50)

Методика

A solution of 2,3,5-trimethylphenol (13.6 g, 100 mmol,) in dichloromethane (20 mL) was ice-cooled, titanium tetrachloride (41.7 g, 220 mmol) was added dropwise over 0.5 hr under nitrogen atmosphere, and the reaction mixture was stirred for 1 hr. Dichloromethyl methyl ether (11.5 g, 100 mmol) was added dropwise, and the mixture was further stirred for 6 hr. The reaction mixture was treated with saturated aqueous ammonium chloride solution, and extracted with dichloromethane. The extract was washed successively with diluted hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-50:50) to give the title compound (6.58 g, yield 40%) as pale-brown crystals.

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