Water → HCID 86748987, compound

HRID 2399888Notes

Reaction equation

HRID 2399888 reaction equation
O.[C:2]1([CH3:29])[CH:7]=[CH:6][C:5]([C:8]([O:10][C:11](=[O:28])[C@@H:12]([C@H:14]([C:16]([O:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)=[O:20])=[O:17])[OH:15])[OH:13])=[O:9])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[OH2:9].[C:2]1([CH3:29])[CH:3]=[CH:4][C:5]([C:8]([O:10][C:11](=[O:28])[C@@H:12]([C@H:14]([C:16]([O:18][C:19]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)=[O:20])=[O:17])[OH:15])[OH:13])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 962WaterHCID 14721060bis(4-methylbenzoyl) (2R,3R)-2,3-dihydroxybutanedioate

Product 1

HCID 86748987HCID 86748987, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
63 °C

Procedure

To a 300 ml reaction vessel equipped with a stirrer, thermometer and a condenser, 50 g of O,O'-di-p-toluoyl-L-tartaric anhydride and 150 g of water were supplied and the mixture was stirred at 90°-95° C. for 1 hour to carry out hydrolysis. After cooling the reaction mixture to 63° C., 5 g of toluene and 0.1 g of seed crystal of O,O'-di-p-toluoyl-L-tartaric acid were added and the mixture was slowly cooled. Since oily product began to crystalize at 61° C., the mixture was stirred for 1 hour at this temperature. After completion of crystallization, the reaction slurry was cooled to room temperature and the crystals were collected by filtration. The thus obtained cake was dried to obtain 52.7 g of O,O'-di-p-toluoyl-L-tartaric acid hydrate in the form of white crystals. The content of crystal water was measured by Karl Fischer method, which was 4.3% (yield: 96.2%). The crystals were sieved through a 20-mesh sieve and 98 wt % of the crystals passed through the sieve. The amount of the crystals which adhered to the wall or to the stirrer of the reaction apparatus so that which could not be removed from the reaction apparatus was 0.8 g which was 1.5 wt % of the total crystals produced.

Workup

  1. customTo a 300 ml reaction vessel
  2. customequipped with a stirrer
  3. customhydrolysis
  4. temperaturethe mixture was slowly cooled
  5. customto crystalize at 61° C.
  6. stirringthe mixture was stirred for 1 hour at this temperature
  7. customAfter completion of crystallization
  8. temperaturethe reaction slurry was cooled to room temperature
  9. filtrationthe crystals were collected by filtration
  10. customThe thus obtained cake was dried

Sources & evidence

ORD record
ord-905835ded92a4533bd1a87ce5b4e1279
Source dataset
uspto-grants-1995_09
Patent number
US05451687

Reaction notes

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