Cyclohexanone → HCID 2724782, compound

HRID 542915Notes

Reaction equation

HRID 542915 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].[Sb](Cl)(Cl)(Cl)(Cl)Cl>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]1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 24294Antimony pentachlorideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 2724782HCID 2724782, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
68 °C

Procedure

To a mixed solution consisting of 150 ml of cyclohexanone and 120 ml of dichloromethane were added 10.0 g of D-glucose and 299 mg of antimony pentachloride, and the mixture was refluxed with stirring in a water bath of 68° C. for 8 hours. During this reaction, the refluxing solvent was dried with 35 g of Molecular Sieves 3A interposed between the reaction vessel and the condenser. After completion of the reaction, 1.71 g of the starting sugar was recovered by filtration, and the reaction solution was diluted with chloroform, washed with aqueous sodium bicarbonate and water, and subsequently dried over anhydrous magnesium sulfate. The solvents including cyclohexanone were distilled off under reduced pressure, and the residue was recrystallized from ligroin to give 12.6 g (66.4%) of 1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose, m.p. 133°-136° C.

Workup

  1. temperaturethe mixture was refluxed
  2. customDuring this reaction
  3. dry with materialthe refluxing solvent was dried with 35 g of Molecular Sieves 3A
  4. customAfter completion of the reaction, 1.71 g of the starting sugar
  5. filtrationwas recovered by filtration
  6. additionthe reaction solution was diluted with chloroform
  7. washwashed with aqueous sodium bicarbonate and water
  8. dry with materialsubsequently dried over anhydrous magnesium sulfate
  9. distillationwere distilled off under reduced pressure
  10. customthe residue was recrystallized from ligroin

Sources & evidence

ORD record
ord-ee4ffd44c47e4c5193c5ca7ef96ab6e4
Source dataset
uspto-grants-1987_04
Patent number
US04659809

Reaction notes

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