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

HRID 4733ノート

反応式

HRID 4733 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2a2734eb88c143a38c09acebdd4195a1
出典データセット
uspto-grants-1988_02
特許番号
US04727181

反応ノート

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