Menthol → menthyl methacrylate
Reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH:7]1([CH3:17])[CH2:12][CH2:11][CH:10]([CH:13]([CH3:15])[CH3:14])[CH:9](O)[CH2:8]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([O:6][CH:9]1[CH:10]([CH:13]([CH3:15])[CH3:14])[CH2:11][CH2:12][CH:7]([CH3:17])[CH2:8]1)(=[O:5])[C:2]([CH3:4])=[CH2:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
24 g of methacrylic acid, 31 g of menthol and 15 g of p-toluenesulfonic acid in 500 mL of toluene were heated under reflux at a oil temperature of 150° C. for 19 h. Subsequently, the reaction mixture was quenched by the addition of salt saturated sodium bicarbonate, solution. The mixture was extracted with ether, the organic layers were combined and washed with salt saturated sodium bicarbonate solution and then with an aqueous solution of sodium hydroxide, salt saturated ammonium chloride solution, then dried over salt saturated brine and sodium sulfate anhydrous. Finally, the resultant oily product was evaporated under reduced pressure to obtain menthyl methacrylate.
Workup
- customSubsequently, the reaction mixture was quenched by the addition of salt saturated sodium bicarbonate, solution
- extractionThe mixture was extracted with ether
- washwashed with salt saturated sodium bicarbonate solution
- dry with materialwith an aqueous solution of sodium hydroxide, salt saturated ammonium chloride solution, then dried over salt saturated brine and sodium sulfate anhydrous
- customFinally, the resultant oily product was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-33366f5197824583b819b2c1f7c64ffd
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06060207
Reaction notes
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