Benzoyl chloride → glucopyranose pentabenzoate
Reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1.O>[C:13]([O:1][CH:2]1[O:10][C@H:9]([CH2:11][O:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:7]([O:8][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:5]([O:6][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:3]1[O:4][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
100 g of D-glucose (555 mmol; 1 eq) are dissolved in 2 l of pyridine and the reaction medium is heated under reflux for 1 hour before 387 ml (3,330 mmol; 6 eq) of benzoyl chloride are added thereto in the hot. After addition, the medium is diluted with water, the product precipitates and is filtered off and rinsed with water to neutrality. After drying, it is purified by recrystallisation from ethyl acetate.