Hydrochloric Acid → HCID 178491465, compound
Reaction equation
[CH2:1]([O:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].C#C.Cl.[Cl:34][CH:35](Cl)[CH3:36]>>[CH2:1]([O:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[CH:19]=[CH:20][C:21]([C:22](=[O:23])[CH:36]=[CH:35][Cl:34])=[CH:25][CH:26]=2)[CH2:14][CH2:13]1)[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1Participants
Procedure
A solution of 16.3 g of p-[trans-4-(p-anisyloxymethyl)-cyclohexyl]benzoyl chloride in 50 ml of dichloroethane is cooled to 7° C. and treated portionwise under nitrogen within 5 minutes with 6.4 g of powdered aluminium chloride. A weak stream of acetylene gas is then conducted through the reaction mixture at 45° C. for 17 hours. The reaction mixture is subsequently poured into 100 ml of ice-water, treated with 50 ml of 3N hydrochloric acid and stirred for 10 minutes. The mixture is extracted with diethyl ether. The organic phase is washed in succession with water, with 5 percent potassium hydroxide solution and several times with water, then dried over magnesium sulphate and evaporated. The trans-4-(p-anisyloxymethyl)-1-[p-(3-chloroacryloyl)phenyl]cyclohexane obtained is purified by chromatography on silica gel.
Workup
- extractionThe mixture is extracted with diethyl ether
- washThe organic phase is washed in succession with water, with 5 percent potassium hydroxide solution and several times with water
- dry with materialdried over magnesium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-968446f175f04488a3ddecd60f3eef6d
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04898455
Reaction notes
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