Cyclohexanone → HCID 2724782, compound
Reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=[CH:9][C@@H:10]([C@H:12]([C@@H:14]([C@@H:16]([CH2:18][OH:19])[OH:17])[OH:15])[OH:13])[OH:11]>ClCCl>[CH2:4]1[CH2:5][CH2:6][C:1]2([O:11][CH:10]([C@H:12]3[O:13][C@@H:18]4[O:19][C:1]5([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)[O:17][C@@H:16]4[C@H:14]3[OH:15])[CH2:9][O:7]2)[CH2:2][CH2:3]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 63 °C
Procedure
To a mixed solution of 150 ml of cyclohexanone and 120 ml of dichloromethane were added 10.0 g of D-glucose and 125 mg of anhydrous cupric chloride, and the mixture was stirred for 8.5 hours under reflux in a warm-water bath at 63° C. The refluxing solvent was continuously dried with 20 g of molecular sieves 3A which was placed between the reaction vessel and the cooling tube. The reaction solution was diluted with chloroform, washed with aqueous sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate. The solvent and cyclohexanone were distilled off under reduced pressure, and the residue was recrystallized from ligroin, thus affording 9.6 g (51%) of 1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose. m.p. 133°-136° C.
Workup
- temperatureunder reflux in
- dry with materialThe refluxing solvent was continuously dried with 20 g of molecular sieves 3A which
- additionThe reaction solution was diluted with chloroform
- washwashed with aqueous sodium hydrogencarbonate and water
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent and cyclohexanone were distilled off under reduced pressure
- customthe residue was recrystallized from ligroin
Sources & evidence
- ORD record
- ord-13c43d55eb2c41dcbf97a03d4b595e94
- Source dataset
- uspto-grants-1984_07
- Patent number
- US04460767
Reaction notes
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