Reaction equation
[CH2:1]([OH:13])[C@H:2]([OH:12])[C@@H:3]([OH:11])[C@H:4]([OH:10])[C:5]([C:7]([OH:9])=[O:8])=[O:6].OCC([C@H]([C@@H]([C@H](CO)O)O)O)=O.[N+]([O-])(O)=O>>[CH2:1]([OH:13])[C:2]([C@@H:3]([OH:11])[C@H:4]([OH:10])[C:5]([C:7]([OH:9])=[O:8])=[O:6])=[O:12]Participants
Procedure
2-Keto-L-Gulonic acid is an important intermediate in vitamin C manufacture. Condensation of L-sorbose with acetone in the presence of sulfuric acid followed by oxidation with permanganate and hydrolysis of the diisopropylidene derivative by boiling yields 2-keto-L-gulonic acid as described in Helv. Chim. Acta. 17, 311 (1934) and U.S. Pat. No. 2,301,811. The preparation of 2-keto-L-gulonic acid by careful oxidation of L-sorbose with nitric acid is claimed in British Pat. No. 443,901 and Dutch Pat. No. 59,584. The selective reduction of 2,5-diketogluconic acid to yield a mixture of 2-ketogluconic acid and 2-ketogulonic acid with subsequent hydrolysis of the 2-ketogulonic acid to afford ascorbic acid is described in co-pending application, Ser. No. 843,946, filed Oct. 20, 1977.
Sources & evidence
- ORD record
- ord-d33d31b97d5a4d37a9d2cbb5d9eac8b2
- Source dataset
- uspto-grants-1980_05
- Patent number
- US04202942
Linked notes
Loading…