Hydrochloric Acid → z-Methyl-2-chloro-3-(4'-chlorophenyl)propenoate

HRID 4734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 4734
[Cl:1]C1C=CC(C(C(Cl)=C(Cl)Cl)O)=CC=1.Cl.[CH3:16][O:17][C:18](=[O:30])/[C:19](/[Cl:29])=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24](OC)=[CH:23][CH:22]=1>>[CH3:16][O:17][C:18](=[O:30])/[C:19](/[Cl:29])=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([Cl:1])=[CH:23][CH:22]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 12339865z-Methyl-2-chloro-3-(4'-methoxyphenyl)propenoateHCID 15054140p-Chlorophenyltrichlorovinyl carbinol

Produkt 1

HCID 13737728z-Methyl-2-chloro-3-(4'-chlorophenyl)propenoateAusbeute 93 %

Versuchsvorschrift

p-Chlorophenyltrichlorovinyl carbinol (6.0 g, 22.0 millimoles) is added to a refluxing solution of methanolic sulfuric acid (30 ml as noted in Example 4). Hydrogen chloride evolution is noted during the stirring procedure for 45 minutes. The mixture is cooled and has a workup as in Example 4, which affords z-methyl-2-chloro-3-(4'-chlorophenyl)propenoate (4.7 g, 20.4 millimoles) in 93 percent yield (M.P.=78° C.-80° C.): 'H NMR (CDCl3) δ 7.77 (1H, s), 7.45 (4H, ab quartet), 3.81 (3H, s); 13C NMR (CDCl3) δ 163.5, 136.1, 135.8, 131.6, 131.3, 128.8, 122.3, 53.4. Analysis calculated for: C, 52.01; H, 3.50. Found: C, 51.85; H, 3.42.

Aufarbeitung

  1. temperatureThe mixture is cooled

Quellen und Nachweise

ORD-Eintrag
ord-0456d0b63d08430e9b2503ac98653c65
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727181

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