Acetic Acid → L-Fructose
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
- temperatureheated at 70° C. for 15 hours
- filtrationThe salt was filtered off
- customThe salt was removed by ethanol precipitation
- filtrationAfter filtration
- concentrationthe filtrate was concentrated
- washeluted with water
- 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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