3,4-Difluorobenzoyl chloride → HCID 178444574、化合物

HRID 2309669ノート

反応式

HRID 2309669 の反応式
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[F:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[F:23])[C:17](Cl)=[O:18]>N1C=CC=CC=1.C1(C)C=CC=CC=1.O>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9]([O:12][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:22]([F:23])=[C:14]([F:13])[CH:15]=2)[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

参加物

6

反応物 2

HCID 27245193,4-Difluorobenzoyl chlorideHCID 178444573HCID 178444573、化合物

生成物 1

HCID 178444574HCID 178444574、化合物収率 70%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

To a solution of trans-4-pentylcyclohexanol (1.9 g 0.011 mol) dissolved in dry pyridine (5 ml) was added a solution of 3,4-difluorobenzoyl chloride (2.0 g, 0.011 mol) dissolved in dry toluene (10 ml), followed by heating the mixture at 60° C. for 3 hours, thereafter pouring the reaction mixture in water (100 ml), separating the toluene layer, washing it with 6N hydrochloric acid, then with 2N-NaOH aqueous solution and further with water, drying with anhydrous sodium sulfate, distilling off toluene from the resulting toluene solution and recrystallizing the remaining oily product from ethanol to obtain the objective 3,4-difluorobenzoic acid-trans-4-pentylcyclohexyl ester (2.4 g, 0.0077 mol) (yield: 70%). This product has a m.p. of 26.9° C., and its N-I point sought from a mixture thereof with trans-4-alkyl-(4-cyanophenyl)cyclohexanes according to extrapolation method was -6.0° C. Further its elemental analysis values were as follows: C: 70.03%, H: 7.81% (calculated values, C: 69.65% and H: 7.79%).

後処理

  1. customseparating the toluene layer
  2. washwashing it with 6N hydrochloric acid
  3. dry with materialwith 2N-NaOH aqueous solution and further with water, drying with anhydrous sodium sulfate
  4. distillationdistilling off toluene from the resulting toluene solution
  5. customrecrystallizing the remaining oily product from ethanol

出典と根拠

ORDレコード
ord-baaa3c427b084013b72c2aed22a11d74
出典データセット
uspto-grants-1987_09
特許番号
US04696759

反応ノート

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