Toluene → HCID 13756210, compound
Reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH:9]1([CH3:19])[CH2:14][CH2:13][CH:12]([CH:15]([CH3:17])[CH3:16])[CH:11]([OH:18])[CH2:10]1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23](S(O)(=O)=O)=[CH:22][CH:21]=1.[C:31]1(C)[CH:36]=CC=C[CH:32]=1>>[CH:9]1([CH3:19])[CH2:14][CH2:13][CH:12]([CH:15]([CH3:17])[CH3:16])[CH:11]([O:5][C:4](=[O:6])/[CH:3]=[CH:2]\[C:1]([OH:8])=[O:7])[CH2:10]1.[C:1]([O:8][CH:22]1[CH:23]([CH:31]([CH3:36])[CH3:32])[CH2:24][CH2:25][CH:20]([CH3:30])[CH2:21]1)(=[O:7])/[CH:2]=[CH:3]\[C:4]([O:18][CH:11]1[CH:12]([CH:15]([CH3:16])[CH3:17])[CH2:13][CH2:14][CH:9]([CH3:19])[CH2:10]1)=[O:6]Participants
6
Conditions
- Temperature
- 150 °C
Procedure
16 g of maleic acid, 20 g of menthol and 10 g of p-toluenesulfonic acid in 30 mL of toluene were heated to reflux at a oil temperature of 150° C. for 10 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, salt saturated ammonium chloride solution, and then dried over salt saturated brine and sodium sulfate anhydrous. Finally, the resultant oily product was subjected to fractional distillation to obtain maleic acid monomenthyl ester and dimenthyl maleate.
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, salt saturated ammonium chloride solution
- dry with materialdried over salt saturated brine and sodium sulfate anhydrous
- distillationFinally, the resultant oily product was subjected to fractional distillation
Sources & evidence
- ORD record
- ord-1b73f18c614b40979f8f66a80cec8404
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06060207
Reaction notes
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