Реакция #4829

Уравнение реакции

p-Methoxyphenyltrichlorovinyl carbinol

sulfuric acid methanol

hydrogen chloride

→

z-methyl-2-chloro-3-(4'-methoxyphenyl)propenoate

Выход 99.0%

Растворители

water

Условия реакции

Обработка

1. 1
   Температураat reflux (100° C.-106° C.) for 7 minutes
2. 2
   workup.WAITceases after this period
3. 3
   ТемператураThe solution is cooled
4. 4
   Экстракцияfollowed by extraction twice with 20 ml of methylene chloride each time
5. 5
   СушкаThe organic phase is dried over MgSO4
6. 6
   Фильтрацияfiltered
7. 7
   Другоеrotary evaporated

Методика

p-Methoxyphenyltrichlorovinyl carbinol (2.3 g, 8.6 millimoles) is added to a 40:60 (V/V) solution of sulfuric acid/methanol which is stirred under nitrogen at reflux (100° C.-106° C.) for 7 minutes. Rapid evolution of hydrogen chloride is noted and ceases after this period. The solution is cooled and poured into 40 ml of water, followed by extraction twice with 20 ml of methylene chloride each time. The organic phase is dried over MgSO4, filtered and rotary evaporated giving z-methyl-2-chloro-3-(4'-methoxyphenyl)propenoate (1.92 g, 8.5 millimoles) in 99 percent yield as a light yellow oil which crystallized on standing (M.P.=68° C.-70° C., M.P.LIT1 =67° C.-70° C.): 'H NMR (CDCl3) δ 7.24 (4H, ab quartet), 7.72 (1H, s), 3.76 (3H, s), 3.68 (3H, s); 13C NMR (CDCl3) δ 164.0, 161.1, 136.7, 132.6, 125.4, 119.0, 113.9, 55.2, 53.0.

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