Реакция #339346

Уравнение реакции

sodium nitrite

sulphuric acid

3-chloro-2-methylaniline

→

desired product

Выход 83.0%

3-Chloro-2-methylphenol

Выход 83.0%

Растворители

water

water

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was cooled to 0° C.
2. 2
   Температураto warm to ambient temperature over 2 h
3. 3
   ДругоеExcess sodium nitrite was destroyed by the addition of urea
4. 4
   workup.ADDITIONThe resultant mixture was added to a solution of concentrated sulphuric acid (5.0 mL) in water (55 mL)
5. 5
   Температураheated to 90° C.
6. 6
   ФильтрацияThe resultant product mixture was filtered through dicalite
7. 7
   Экстракцияextracted with dichloromethane (2×200 mL)
8. 8
   ПромывкаThe organic phase was washed with NaHCO3 (aq.)
9. 9
   Сушкаdried (MgSO4)
10. 10
    Другоеevaporated under reduced pressure

Методика

A solution of concentrated sulphuric acid (7.3 mL) in water (97 mL) was added to 3-chloro-2-methylaniline (0.84 mL, 7.06 mmol) and the mixture heated at 90° C. until solution was achieved. The reaction mixture was cooled to 0° C. and a solution of sodium nitrite (510 mg, 12.75 mmol) in water (5 mL) was added dropwise. The reaction mixture was allowed to warm to ambient temperature over 2 h. Excess sodium nitrite was destroyed by the addition of urea. The resultant mixture was added to a solution of concentrated sulphuric acid (5.0 mL) in water (55 mL), heated to 90° C. and stirred at this temperature for a further 1 h. The resultant product mixture was filtered through dicalite and extracted with dichloromethane (2×200 mL). The organic phase was washed with NaHCO3 (aq.), dried (MgSO4) and evaporated under reduced pressure to afford the desired product (830 mg, 83%) as an off-white solid.

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