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

HRID 4734Notes

Reaction equation

HRID 4734 reaction equation
[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

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 12339865z-Methyl-2-chloro-3-(4'-methoxyphenyl)propenoateHCID 15054140HCID 15054140, compound

Product 1

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

Procedure

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.

Workup

  1. temperatureThe mixture is cooled

Sources & evidence

ORD record
ord-0456d0b63d08430e9b2503ac98653c65
Source dataset
uspto-grants-1988_02
Patent number
US04727181

Reaction notes

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