Water → HCID 86748992, compound

HRID 2399892Notes

Reaction equation

HRID 2399892 reaction equation
O.[Cl:2][C:3]1[CH:29]=[CH:28][CH:27]=[CH:26][C:4]=1[C:5]([O:7][C:8](=[O:25])[C@@H:9]([C@H:11]([C:13]([O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])=[O:14])[OH:12])[OH:10])=[O:6]>C1(C)C=CC=CC=1>[OH2:6].[Cl:2][C:3]1[CH:29]=[CH:28][CH:27]=[CH:26][C:4]=1[C:5]([O:7][C:8](=[O:25])[C@@H:9]([C@H:11]([C:13]([O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])=[O:14])[OH:12])[OH:10])=[O:6]

Participants

4

Reactant 2

HCID 962WaterHCID 86748993HCID 86748993, compound

Product 1

HCID 86748992HCID 86748992, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
43 °C

Procedure

To the reaction vessel employed in Example 30, 50 g of O,O'-bis(o-chlorobenzoyl)-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 43° C., 5 g of toluene and 0.1 g of seed crystal of O,O'-bis(o-chlorobenzoyl)-L-tartaric acid were added and the mixture was slowly cooled. Since oily product began to crystalize at 39° 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 51.7 g of O,O'-bis(o-chlorobenzoyl)-L-tartaric acid hydrate in the form of white crystals. The content of crystal water was measured by Karl Fischer method, which was 4.8% (yield: 94.3%). The crystals were sieved through a 20-mesh sieve and 95 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 1.9 g which was 3.5 wt % of the total crystals produced.

Workup

  1. customhydrolysis
  2. temperaturethe mixture was slowly cooled
  3. customto crystalize at 39° C.
  4. stirringthe mixture was stirred for 1 hour at this temperature
  5. customAfter completion of crystallization
  6. temperaturethe reaction slurry was cooled to room temperature
  7. filtrationthe crystals were collected by filtration
  8. customThe thus obtained cake was dried

Sources & evidence

ORD record
ord-24dd126628af41d48435947f897e74e1
Source dataset
uspto-grants-1995_09
Patent number
US05451687

Reaction notes

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