P-Toluic Acid → (3S,4S)-2,5-Dioxooxolane-3,4-diyl bis(4-methylbenzoate)

HRID 2399884Notes

Reaction equation

HRID 2399884 reaction equation
[C:1]([OH:10])(=[O:9])[C@H:2]([C@@H:4]([C:6]([OH:8])=O)[OH:5])[OH:3].[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([OH:20])=O)=[CH:16][CH:17]=1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:3][C@@H:2]2[C:1](=[O:9])[O:10][C:6](=[O:8])[C@H:4]2[O:5][C:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:11])=[CH:13][CH:14]=2)=[O:20])=[O:20])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7470P-Toluic AcidHCID 24386Thionyl ChlorideHCID 439655D-Tartaric acid

Product 1

HCID 56604168(3S,4S)-2,5-Dioxooxolane-3,4-diyl bis(4-methylbenzoate)Yield 91.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 and 59.9 g of p-toluic acid were supplied, and the mixture was heated to 90° C. While keeping this temperature, 83.7 g of thionyl chloride was added from the dropping funnel for 6 hours and the resulting mixture was aged at 105°-110° C. for another 1 hour to carry out the reaction. The reaction mixture was then cooled to room temperature and the precipitated crystals were collected by filtration, followed by drying to obtain 67.2 g of O,O'-di-p-toluoyl-D-tartaric anhydride in the form of pale yellow crystals (purity: 100%, yield: 91.3%).

Workup

  1. customTo a 300 ml reaction vessel
  2. customequipped with a stirrer
  3. additionwas added from the dropping funnel for 6 hours
  4. customthe reaction
  5. temperatureThe reaction mixture was then cooled to room temperature
  6. filtrationthe precipitated crystals were collected by filtration
  7. customby drying

Sources & evidence

ORD record
ord-207923cf7a8a4f409b8a557a2bc13295
Source dataset
uspto-grants-1995_09
Patent number
US05451687

Reaction notes

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