Sulfuric Acid → HCID 59392440, compound

HRID 570860Notes

Reaction equation

HRID 570860 reaction equation
S(=O)(=O)(O)O.[O:6]=[C:7]1[O:13][C@H:12]([C@H:14]([CH2:16][OH:17])[OH:15])[C:10]([OH:11])=[C:8]1[OH:9].[N:18]1[N:19]([C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=2[OH:36])[C:30](O)=[O:31])[N:20]=[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=12.OS(O)(=O)=O.O=S(=O)=O.[Cl-].[Na+]>>[N:18]1[N:19]([C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=2[OH:36])[C:30]([O:17][CH2:16][C@H:14]([C@@H:12]2[C:10]([OH:11])=[C:8]([OH:9])[C:7](=[O:6])[O:13]2)[OH:15])=[O:31])[N:20]=[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=12

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 24681Fuming sulfuric acidHCID 13000698HCID 13000698, compoundHCID 54670067L-Ascorbic Acid

Product 1

HCID 59392440HCID 59392440, compound

Conditions

Temperature
0 °C

Procedure

265 ml of conc. sulfuric acid are initially introduced in an argon-flushed 3-necked flask and cooled to 0° C. 124.2 g (0.705 mol, 3 eq.) of ascorbic acid and subsequently 60 g of 3-benzotriazol-2-yl-4-hydroxybenzoic acid (0.235 mol, 1 eq.) are added in portions. 73.7 ml of oleum (sulfuric acid containing 65% of SO3) are then added dropwise. After a reaction time of 5 hrs. at 45° C., the reaction solution is poured onto 1000 g of ice, saturated with 200 g of sodium chloride and extracted 3× with 1000 ml of ethyl methyl ketone. The combined org. phases are extracted with 500 ml of sat. NaCl solution, dried over sodium sulfate, and the solvent is removed in vacuo. Crystallisation from ethyl acetate gives the product as a white solid.

Workup

  1. customflushed 3-necked flask
  2. customAfter a reaction time of 5 hrs
  3. extractionextracted 3× with 1000 ml of ethyl methyl ketone
  4. extractionphases are extracted with 500 ml of sat. NaCl solution
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is removed in vacuo
  7. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-737ed6b3a11841cbaa74000d70cebc0e
Source dataset
uspto-grants-2015_05
Patent number
US09023889B2

Reaction notes

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