Hydrochloric Acid → HCID 2724782, compound

HRID 1462579Notes

Reaction equation

[CH2:1]([CH2:4]OC)OC.[C:7]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.O=[CH:15][C@@H:16]([C@H:18]([C@@H:20]([C@@H:22]([CH2:24][OH:25])[OH:23])[OH:21])[OH:19])[OH:17].Cl>O1CCOCC1.C1C=CC=CC=1>[CH2:10]1[CH2:11][CH2:12][C:7]2([O:17][CH:16]([C@H:18]3[O:19][C@@H:24]4[O:25][C:4]5([CH2:1][CH2:9][CH2:8][CH2:7][CH2:12]5)[O:23][C@@H:22]4[C@H:20]3[OH:21])[CH2:15][O:13]2)[CH2:8][CH2:9]1

Participants

Conditions

Temperature: 95 °C

Procedure

To a mixed solution of 150 ml of dimethoxyethane and 50 ml of cyclohexanone were added 10.0 g of D-glucose, 150 mg of cupric hydroxide and 1 ml of a 2 mole/l solution of hydrogen chloride in dioxane, and the mixture was stirred for 7 hours under reflux in an oil bath at 95° C. The refluxing solvent was continuously dried with 20 g of molecular sieve 3A which was placed between the reaction vessel and the cooling tube. After the conclusion of the reaction, the reaction solution was diluted with benzene, washed with aqueous sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate. When the solvent and cyclohexanone were distilled off under reduced pressure, there was obtained 15.5 g (82.1%) of 1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose as a residue. The compound, when recrystallized from ligroin, showed a melting point of 133° to 135° C.

Workup

dry with materialThe refluxing solvent was continuously dried with 20 g of molecular sieve 3A which
customAfter the conclusion of the reaction
washwashed with aqueous sodium hydrogencarbonate and water
dry with materialdried over anhydrous magnesium sulfate
distillationWhen the solvent and cyclohexanone were distilled off under reduced pressure

Sources & evidence

ORD record: ord-95ad3096611345f1aca74db4550332fc
Source dataset: uspto-grants-1984_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04460767

Reaction notes

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