Sulfuric Acid → HCID 2724782, compound

HRID 987939Notes

Reaction equation

HRID 987939 reaction equation
S(=O)(=O)(O)O.[O:6]=[CH:7][C@@H:8]([C@H:10]([C@@H:12]([C@@H:14]([CH2:16][OH:17])[OH:15])[OH:13])[OH:11])[OH:9].[C:18]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.O1[CH2:30][CH2:29]OCC1>>[CH2:18]1[CH2:23][CH2:22][C:21]2([O:9][CH:8]([C@H:10]3[O:11][C@@H:16]4[O:17][C:30]5([CH2:29][CH2:12][CH2:10][CH2:8][CH2:7]5)[O:15][C@@H:14]4[C@H:12]3[OH:13])[CH2:7][O:6]2)[CH2:20][CH2:19]1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 7967CyclohexanoneHCID 312751,4-DioxaneHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 2724782HCID 2724782, compoundYield 169.3%

Procedure

20 ml (375 mmol; 1.03 eq) of concentrated sulphuric acid are added dropwise to 65 g of D-glucose (361 mmol; 1 eq) and 85 ml (820 mmol ; 2.27 eq) of cyclohexanone in 50 ml of 1,4-dioxane (587 mmol; 1.62 eq) at ambient temperature. Once the addition is complete, after 30 minutes, the product precipitates from the reaction medium. The precipitate is broken up, filtered off and washed with water. The crude product is then purified by recrystallisation from cyclohexane to give to 104 grams of 1,2: 5,6-di-O-cyclohexylidene-α-D-glucofuranose.

Workup

  1. additionOnce the addition
  2. customthe product precipitates from the reaction medium
  3. filtrationfiltered off
  4. washwashed with water
  5. customThe crude product is then purified by recrystallisation from cyclohexane

Sources & evidence

ORD record
ord-b84a6cb28201421bb1aab38923a4e646
Source dataset
uspto-grants-2003_10
Patent number
US06632940B1

Reaction notes

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