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].I>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
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a mixture of 150 ml of cyclohexanone and 120 ml of dichloromethane were added 10.0 g of D-glucose and 175 mg of hydriodic acid (57%) and the mixture was refluxed with stirring in a water bath at 65° C. for 8 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the cooling jacket. The reaction mixture was diluted with chloroform, washed with aqueous sodium bicarbonate 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 to give 11.2 g (77.8%) of 1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose, melting at 133°-136° C.
Workup
- temperaturethe mixture was refluxed
- customDuring this reaction
- dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A
- additionThe reaction mixture was diluted with chloroform
- washwashed with aqueous sodium bicarbonate 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-a47b9b4a3e014600a779a7c843f441d0
- Source dataset
- uspto-grants-1984_08
- Patent number
- US04464530
Reaction notes
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