P-Toluic Acid → (3S,4S)-2,5-Dioxooxolane-3,4-diyl bis(4-methylbenzoate)
Reaction equation
[C:1]([OH:10])(=[O:9])[C@H:2]([C@@H:4]([C:6]([OH:8])=O)[OH:5])[OH:3].S(Cl)(Cl)=O.[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([OH:24])=O)=[CH:20][CH:21]=1>C1(C)C=CC=CC=1>[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([O:3][C@@H:2]2[C:1](=[O:9])[O:10][C:6](=[O:8])[C@H:4]2[O:5][C:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=2)=[O:24])=[O:24])=[CH:18][CH:17]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a 300 ml reaction vessel equipped with a stirrer, thermometer, condenser and a dropping funnel, 30 g of D-tartaric acid, 70 g of toluene, 0.12 g of ferric chloride, 83.7 g of thionyl chloride and 59.9 g of p-toluic acid were supplied, and the mixture was heated to 90° C. under stirring for 3 hours. While keeping this temperature, the mixture was aged for another 4 hours and the resulting mixture was heated at 105°-110° C. for another 1 hour. The reaction mixture was then cooled to room temperature and the precipitated crystals were collected by filtration, followed by drying to obtain 67.7 g of O,O'-di-p-toluoyl-D-tartaric anhydride in the form of pale yellow crystals (purity: 100%, yield: 92.0%).
Workup
- customTo a 300 ml reaction vessel
- customequipped with a stirrer
- waitthe mixture was aged for another 4 hours
- temperaturethe resulting mixture was heated at 105°-110° C. for another 1 hour
- temperatureThe reaction mixture was then cooled to room temperature
- filtrationthe precipitated crystals were collected by filtration
- customby drying
Sources & evidence
- ORD record
- ord-9724ad9c08984c3e8b55a1198d6292ab
- Source dataset
- uspto-grants-1995_09
- Patent number
- US05451687
Reaction notes
Loading…