p-Toluenesulfonic acid monohydrate → HCID 86745993, compound
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]COC)=[C:19]([O:27]COC)[CH:18]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>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]([OH:27])[CH:18]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 1.96 g of 5-(3',4'-dimethoxymethoxyphenyl)pentadienoic acid geranylamide in 40 ml of methanol is added 0.09 g of p-toluenesulfonic acid monohydrate. The mixture is stirred at 50° C. for 3 hours. The reaction mixture is poured onto water and extracted with chloroform. The organic layer is washed with saturated aqueous sodium chloride and dried over anhydrous 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 chloroform-methanol (99:1) is obtained 1.40 g of 5-(3',4'-dihydroxyphenyl)pentadienoic acid geranylamide (15). Spectroscopic data of the product support the structure of the formula (15) below.
Workup
- additionThe reaction mixture is poured onto water
- extractionextracted with chloroform
- washThe organic layer is washed with saturated aqueous sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent is distilled off under reduced pressure
- washFrom the fraction eluted with chloroform-methanol (99:1)
Sources & evidence
- ORD record
- ord-f78a13984c964f35b9bdff0948d5b0cf
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05130483
Reaction notes
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