反応 #43908

反応方程式

2,3,5-trimethylphenol

Dichloromethyl methyl ether

ammonium chloride

→

title compound

収率 40.1%

2-hydroxy-3,4,6-trimethylbenzaldehyde

収率 40.1%

溶媒

dichloromethane

反応条件

後処理

1. 1
   温度cooled
2. 2
   workup.STIRRINGthe mixture was further stirred for 6 hr
3. 3
   抽出extracted with dichloromethane
4. 4
   洗浄The extract was washed successively with diluted hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated brine
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-50:50)

実験手順

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.

出典