Реакция #65435

Уравнение реакции

ethyl 6-ethyl-2,3-dihydro-1,4-benzodioxin-2-carboxylate

tert-butyl hydroperoxide

→

Ethyl 6-acetyl-2,3-dihydro-1,4-benzodioxin-2-carboxylate

Выход 62.0%

Растворители

methylene chloride

methylene chloride

Условия реакции

Обработка

1. 1
   workup.WAITfor 72 hours at room temperature
2. 2
   ДругоеThe crude product obtained
3. 3
   Концентрированиеby concentrating to dryness
4. 4
   Другоеis purified by chromatography on a silica column (eluant: methylene chloride)

Методика

Add 2 g (8.5 mmol) of ethyl 6-ethyl-2,3-dihydro-1,4-benzodioxin-2-carboxylate dissolved in 5 cm3 of anhydrous methylene chloride to a mixture at 0° C. of 0.042 g (0.42 mmol) of chromium trioxide and 5.35 g (59.3 mmol) of 70% tert-butyl hydroperoxide in 30 cm3 of methylene chloride. Stir for 2 hours at 0° C. and then for 72 hours at room temperature. The crude product obtained by concentrating to dryness is purified by chromatography on a silica column (eluant: methylene chloride). Ethyl 6-acetyl-2,3-dihydro-1,4-benzodioxin-2-carboxylate is thereby obtained in a yield of 62%.

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