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

HRID 4733Notes

Reaction equation

HRID 4733 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11](Cl)=[C:12](Cl)Cl)O)=[CH:5][CH:4]=1.S(=O)(=O)(O)[OH:17].[CH3:21][OH:22].[ClH:23]>O>[CH3:21][O:22][C:12](=[O:17])/[C:11](/[Cl:23])=[CH:9]/[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15054139p-Methoxyphenyltrichlorovinyl carbinolHCID 18363649Sulfuric acid methanol

Product 1

HCID 12339865z-Methyl-2-chloro-3-(4'-methoxyphenyl)propenoateYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. temperatureat reflux (100° C.-106° C.) for 7 minutes
  2. waitceases after this period
  3. temperatureThe solution is cooled
  4. extractionfollowed by extraction twice with 20 ml of methylene chloride each time
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. customrotary evaporated

Sources & evidence

ORD record
ord-2a2734eb88c143a38c09acebdd4195a1
Source dataset
uspto-grants-1988_02
Patent number
US04727181

Reaction notes

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