Hydrochloric Acid → (E)-5-methyl-4-bis(4-fluorophenyl)methylidene-2-hexenoic acid

HRID 2380642노트

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HRID 2380642 반응식
[CH3:1][CH:2]([CH3:26])[C:3](=[C:11]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)/[CH:4]=[CH:5]/[C:6]([O:8]CC)=[O:7].[OH-].[Na+].Cl>C1(C)C=CC=CC=1>[CH3:1][CH:2]([CH3:26])[C:3](=[C:11]([C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)/[CH:4]=[CH:5]/[C:6]([OH:8])=[O:7]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86747465HCID 86747465, 화합물

생성물 1

HCID 18954766(E)-5-methyl-4-bis(4-fluorophenyl)methylidene-2-hexenoic acid수율 78%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
60 °C

실험 절차

A toluene (8 ml) solution of the above ester (2.38 g, 6.7 mmol) was added to powdery sodium hydroxide (0.34 g, 8.5 mmol) under argon atmosphere, and the whole was stirred at 60° C. for 5 hours. The reaction mixture was neutralized with 1M hydrochloric acid (10 ml) and extracted with ethyl acetate (25 ml×3 times). The organic layer was washed with water, saturated sodium chloride aq solution and then dried over anhydrous magnesium sulfate. Concentration of the organic layer in vacuo followed by recrystallization from a mixed solvent (hexane:ethyl acetate=4:1) gave 1.70 g (78% yield) of (E)-5-methyl-4-bis(4-fluorophenyl)methylidene-2-hexenoic acid. mp=225°-230° C. Rf =0.52 (hexane:ethyl acetate=1:1) IR (KBr): 3350, 2400, 3025, 1690, 1615, 1515, 1430, 1320, 1225, 1165, 1100, 1080, 1005, 965, 860, 850, 595, 580 cm-1.

후처리

  1. extractionextracted with ethyl acetate (25 ml×3 times)
  2. washThe organic layer was washed with water, saturated sodium chloride aq solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customConcentration of the organic layer in vacuo followed by recrystallization from a mixed solvent (hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-5b5687f8450141daa202ed89c2bd0268
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05369109

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