Cyclohexanone → HCID 90474078, compound

HRID 358132

Reaction equation

HRID 358132 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][C@@H: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]1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 24841Hydrogen iodideHCID 161658Demannose

Product 1

HCID 90474078HCID 90474078, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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-mannose 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 benzene, washed with aqueous sodium bicarbonate and water and dried over anhydrous magnesium sulfate. The solvent and cyclohexanone were distilled off under reduced pressure to give 11.9 g (82.6%) of 2,3:5,6-di-O-cyclohexylidene-α-D-mannofuranose. After recrystallization from cyclohexane, it melted at 122°-124° C.

Workup

  1. temperaturethe mixture was refluxed
  2. customDuring this reaction
  3. dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A
  4. additionThe reaction mixture was diluted with benzene
  5. washwashed with aqueous sodium bicarbonate and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent and cyclohexanone were distilled off under reduced pressure

Sources & evidence

ORD record
ord-9298289001374aa3a10a92d9fc57faa9
Source dataset
uspto-grants-1984_08
Patent number
US04464530

Linked notes

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