Hydrochloric Acid → 5-(4'-Hydroxy-3-methoxyphenyl)pentadienoic acid geranylamide
Reaction equation
[CH2:1]([NH:11][C:12](=[O:31])[CH:13]=[CH:14][CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23]C(OCC)=O)=[C:19]([O:29][CH3:30])[CH:18]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([NH:11][C:12](=[O:31])[CH:13]=[CH:14][CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([O:29][CH3:30])[CH:18]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4]Participants
Procedure
To a solution of 1.61 g of 5-(4'-ethoxycarbonyloxy-3'-methoxyphenyl)pentadienoic acid geranylamide in 25 ml of methanol is added 10 ml of 2N aqueous solution of sodium hydroxide. The mixture is stirred at room temperature for one hour. The reaction mixture, after acidified with 1N hydrochloric acid, is extracted with chloroform. The organic layer is washed with water and dried over sodium sulfate. The solvent is distilled off under reduced pressure, and the residue is subjected to column chromatography on silica gel. From the fraction eluted with methylene chloride is obtained 1.20 g of 5-(4'-hydroxy-3-methoxyphenyl)pentadienoic acid geranylamide (12). Spectroscopic data of the product support the structure of the formula (12) below.
Workup
- extractionis extracted with chloroform
- washThe organic layer is washed with water
- dry with materialdried over sodium sulfate
- distillationThe solvent is distilled off under reduced pressure
- washFrom the fraction eluted with methylene chloride
Sources & evidence
- ORD record
- ord-dd713cb3697142098f80890c2dcd4e68
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05130483
Reaction notes
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