Sulfuric Acid → HCID 2724782, compound

HRID 2289170Notes

Reaction equation

HRID 2289170 reaction equation
[OH:1][C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].S(=O)(=O)(O)O.[C:18]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>>[CH2:18]1[CH2:23][CH2:22][C:21]2([O:8][CH:7]([C@H:9]3[O:10][C@@H:2]4[O:1][C:18]5([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]5)[O:4][C@@H:3]4[C@H:11]3[OH:12])[CH2:5][O:6]2)[CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7967CyclohexanoneHCID 79025Alpha-D-Glucose

Product 1

HCID 2724782HCID 2724782, compoundYield 29%

Conditions

Temperature
20 °C

Procedure

DCG was prepared according to the procedure described in J. Am. Chem. Soc., 1949, 71, 3072. A mixture of 90 g of α-D-glucose, 200 mL of cyclohexanone and 13 mL of sulfuric acid was allowed to stir at 20° C. for 12 h to afford 43.9 g (29%) of the above-titled compound, after two crystallizations: mp.=130.5-131.5° C. (lit. 131.1-132.4° C.).

Workup

  1. customDCG was prepared

Sources & evidence

ORD record
ord-e86b0fb270c04e68b7abfdf28444159a
Source dataset
uspto-grants-2000_07
Patent number
US06090950

Reaction notes

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