반응 #4829

반응 방정식

p-Methoxyphenyltrichlorovinyl carbinol

sulfuric acid methanol

hydrogen chloride

→

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

수율 99.0%

용매

water

반응 조건

후처리

1. 1
   온도at reflux (100° C.-106° C.) for 7 minutes
2. 2
   workup.WAITceases after this period
3. 3
   온도The solution is cooled
4. 4
   추출followed by extraction twice with 20 ml of methylene chloride each time
5. 5
   건조The organic phase is dried over MgSO4
6. 6
   여과filtered
7. 7
   기타rotary evaporated

실험 절차

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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