Ammonia → 3-(4-Hydroxy-3-methoxyphenyl)-2-methylprop-2-enoic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][C:14]=1[O:15]C(=O)CC)[CH:6]=[C:7]([CH3:11])[C:8]([OH:10])=[O:9].N>O1CCOCC1>[OH:15][C:14]1[CH:13]=[CH:12][C:5]([CH:6]=[C:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[O:2][CH3:1]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To cycloartenyl ester of 3-methoxy-4-propionyloxy-α-methyl-cinnamic acid (84.0 g, 0.125 mole) prepared according to the procedure of Example 113 dissolved in dioxane (1000 ml) was added 25% aqueous ammonia (200 ml) and the solution was stirred at 50° C. for 2 hours. Then, the reaction mixture was concentrated under reduced pressure to remove the solvent, and the residue was dissolved in chloroform. The chloroform solution was washed with saturated brine (500 ml), and the aqueous layer were extracted with chloroform (300 ml×2). The combined chloroform layer was dried, concentrated under reduced pressure, and the residue was recrystallized from methylene chloride-methanol (1:4, v/v), giving cycloartenyl ester of 4-hydroxy-3-methoxy-α-methylcinnamic acid (73.0 g), in a yield 94.8%. m.p.143°-144° C.
Workup
- concentrationThen, the reaction mixture was concentrated under reduced pressure
- customto remove the solvent
- dissolutionthe residue was dissolved in chloroform
- washThe chloroform solution was washed with saturated brine (500 ml)
- extractionthe aqueous layer were extracted with chloroform (300 ml×2)
- dry with materialThe combined chloroform layer was dried
- concentrationconcentrated under reduced pressure
- customthe residue was recrystallized from methylene chloride-methanol (1:4, v/v)
Sources & evidence
- ORD record
- ord-2f44f026746040f4adfa4c2259b2f1ae
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04748161
Reaction notes
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