Acetic Acid → L-Fructose

HRID 1731867Notes

Reaction equation

HRID 1731867 reaction equation
[OH-:1].[Na+].S(=O)(=O)(O)O.[C:8]([OH:11])(=O)[CH3:9]>>[OH:1][CH2:9][C:9]([C@@H:8]([C@H:8]([C@H:9]([CH2:8][OH:11])[OH:1])[OH:11])[OH:11])=[O:1]

Participants

4

Conditions

Temperature
40 °C

Procedure

Compound 3 (3 g) dissolved in 60% acetic acid (30 ml) was heated at 40° C. for 3 hours. The mixture was made alkaline with 10N sodium hydroxide solution (40 ml), heated at 70° C. for 15 hours and then acidified with 18N sulfuric acid solution (30 ml). The salt was filtered off and the filtrate left at room temperature for 18 hours and 70° C. for 2 hours. The mixture was neutralized with 10N sodium hydroxide solution (3.5 ml). The salt was removed by ethanol precipitation. After filtration, the filtrate was concentrated, deionized with a column of Amberlite MG-1 ion-exchange resin, and eluted with water. The effluent was concentrated to give L-fructose as a syrup (1.21 g, 76%).

Workup

  1. temperatureheated at 70° C. for 15 hours
  2. filtrationThe salt was filtered off
  3. customThe salt was removed by ethanol precipitation
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. washeluted with water
  7. concentrationThe effluent was concentrated

Sources & evidence

ORD record
ord-ac722c77069c451daabfa52be98bd855
Source dataset
uspto-grants-1986_11
Patent number
US04623721

Reaction notes

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