Methacrylic Acid → 3,7-Dimethyloct-6-en-1-yl 2-methylprop-2-enoate
Reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:7][C:8](=[CH:10][CH2:11][CH2:12][CH:13]([CH2:15][CH2:16]O)[CH3:14])[CH3:9].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([O:6][CH2:16][CH2:15][CH:13]([CH2:12][CH2:11][CH:10]=[C:8]([CH3:9])[CH3:7])[CH3:14])(=[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 citronellol and 1.5 g of p-toluenesulfonic acid in 500 mL of toluene were heated to 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 mixed solution was extracted with ether. The organic layers were combined and washed with salt saturated sodium bicarbonate solution, an aqueous solution of sodium hydride, and then salt saturated ammonium chloride solution, and then dried over salt saturated brine and sodium sulfate anhydrous. Finally, the resultant oily product was evaporated under reduced pressure to obtain citronellyl methacrylate.
Workup
- customSubsequently, the reaction mixture was quenched by the addition of salt saturated sodium bicarbonate solution
- extractionThe mixed solution was extracted with ether
- washwashed with salt saturated sodium bicarbonate solution
- dry with materialan aqueous solution of sodium hydride, and then salt saturated ammonium chloride solution, and 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-5a251c0ccdd143b1baf0e96d08592250
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06060207
Reaction notes
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