p-Toluenesulfonic acid → HCID 70267956, compound
Reaction equation
[CH:1]1([CH3:18])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([O:10][C:11](=[O:17])/[CH:12]=[CH:13]\[C:14]([OH:16])=[O:15])[CH2:2]1.[CH3:19][C:20](O)([CH3:22])[CH3:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:20]([O:15][C:14](/[CH:13]=[CH:12]\[C:11]([O:10][CH:3]1[CH:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH2:6][CH:1]([CH3:18])[CH2:2]1)=[O:17])=[O:16])([CH3:22])([CH3:21])[CH3:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
2.5 g of maleic acid monomenthyl ester, 1 g of 2-methyl-2-propanol and 0.7 g of p-toluenesulfonic acid in 30 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 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, and then dried over salt saturated brine and sodium sulfate anhydrous. Finally, the resultant oily product was subjected to distillation under reduced pressure to obtain menthyl 3-t-butoxycarbonyl-2Z-propenoate.
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, and then dried over salt saturated brine and sodium sulfate anhydrous
- distillationFinally, the resultant oily product was subjected to distillation under reduced pressure
Sources & evidence
- ORD record
- ord-0f2f0c2b1abb46e081fea8a85a385540
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06060207
Reaction notes
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