Hydrochloric Acid → HCID 178448013、化合物

HRID 1731279ノート

反応式

HRID 1731279 の反応式
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22](=[O:24])C)=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[OH-].[Na+].BrBr.[OH:29]S([O-])=O.[Na+].Cl>O1CCOCC1.O.C(Cl)Cl>[CH2:1]([C@H:4]1[CH2:5][CH2:6][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([OH:29])=[O:24])=[CH:20][CH:21]=3)[CH2:12][CH2:11]2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 23665763Sodium BisulfiteHCID 178448005HCID 178448005、化合物

生成物 1

HCID 178448013HCID 178448013、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 32.6 g of p-(trans-4-(trans-4-propyl-cyclohexyl)-cyclohexyl)-acetophenone in 100 ml of dioxane is added dropwise to a solution of 40 g of NaOH and 48 g of bromine in 230 ml of water at 20°, while stirring. Stirring is continued for 1 hour. A solution of 14 g of NaHSO3 in 140 ml of water is added and hydrochloric acid is added until the pH is 5. Customary working up (CH2Cl2) gives p-(trans-4-(trans-4-propylcyclohexyl)-cyclohexyl)-benzoic acid. The crude product is boiled with 60 ml of SOCl2 for 2.5 hours. After evaporation, the resulting crude acid chloride is dissolved in 430 ml of dioxane, 200 ml of 25% aqueous ammonia is added and the mixture is poured onto ice and filtered to give p-(trans-4-(trans-4-propylcyclohexyl)-cyclohexyl)-benzamide. 65 g of POCl3 is added dropwise to a solution of 32.7 g of this amide in 500 ml of DMF at 50°, while stirring. After the mixture has been further stirred for 1 hour, it is poured onto ice and worked up in the customary manner (CH2Cl2) to give trans-1-p-cyanophenyl-4-(trans-4-propyl-cyclohexyl)-cyclohexane, m.p. 55°, c.p. 184°.

後処理

  1. stirringStirring

出典と根拠

ORDレコード
ord-24724ded2e8349678e1cf5e4cec821e3
出典データセット
uspto-grants-1986_11
特許番号
US04620938

反応ノート

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