Hydrochloric Acid → (E)-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzoic acid

HRID 1502807ノート

反応式

HRID 1502807 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:24]([F:27])([F:26])[F:25])/[CH:10]=[CH:11]/[C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[C:14]([CH3:23])[CH:13]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:24]([F:27])([F:25])[F:26])/[CH:10]=[CH:11]/[C:12]2[CH:22]=[CH:21][C:15]([C:16]([OH:18])=[O:17])=[C:14]([CH3:23])[CH:13]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86675123(E)-ethyl 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzoate

生成物 1

HCID 86675124(E)-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzoic acid収率 50%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of (E)-ethyl 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzoate (1.7 g, 4.0 mmol) in 1,4-dioxane (10 mL) was added 11 N HCl (30 mL), and the reaction mixture was heated at 100° C. for 48 h. The reaction mixture was cooled to 25° C. and concentrated under reduced pressure. The residue was diluted with water and extracted with chloroform (CHCl3). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure, and the crude compound was washed with n-hexane to afford the title compound as a white solid (0.7 g, 50%): mp 142-143° C.; 1H NMR (400 MHz, DMSO-d6) δ 12.62 (br s, 1H), 7.81 (d, J=8.0 Hz, 1H), 7.66 (s, 3H), 7.52-7.44 (m, 2H), 6.89 (dd, J=16.0, 8.0 Hz, 1H), 6.78-6.74 (d, J=16.0 Hz, 1H), 4.84 (m, 1H), 2.50 (s, 3H); ESIMS m/z 387.05 ([M−H]−); IR (thin film) 3448, 1701, 1109, 777 cm−1.

後処理

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with chloroform (CHCl3)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. washthe crude compound was washed with n-hexane

出典と根拠

ORDレコード
ord-c4e7b9205a9e49c493b17071e1a6ec6a
出典データセット
uspto-grants-2015_12
特許番号
US09211280B2

反応ノート

読み込み中…