Benzaldehyde → zilascorb

HRID 1583570Notes

Reaction equation

HRID 1583570 reaction equation
[O:1]=[C:2]1[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]([OH:6])=[C:3]1[OH:4].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[Cl-].[Zn+2].[Cl-].O1CCOCC1>[CH2:11]1[O:12][CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:10][C@@H:9]1[C@H:7]1[O:8][C:2](=[O:1])[C:3]([OH:4])=[C:5]1[OH:6]

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 54670067L-Ascorbic Acid

Product 1

HCID 54682464zilascorb

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Ascorbic acid (89.2 g.) was slurried in 400 ml. of p-dioxane, 200 g. of zinc chloride were added slowly and the resulting mixture was stirred for one hour. Next, 100 ml. (104 g.) of benzaldehyde were added. This reaction mixture was stirred at ambient temperature for about 24 hours and was then extracted with 500 ml. of ethyl acetate. The ethyl acetate extract was itself extracted with three portions of saturated aqueous sodium chloride. The ethyl acetate solution was dried and the dried solution treated with activated charcoal and then filtered through cellulose. Concentration of the filtrate caused 5,6-O-benzylidene-L-ascorbic acid to crystallize.

Workup

  1. stirringThis reaction mixture was stirred at ambient temperature for about 24 hours
  2. extractionwas then extracted with 500 ml
  3. extractionThe ethyl acetate extract
  4. extractionextracted with three portions of saturated aqueous sodium chloride
  5. dry with materialThe ethyl acetate solution was dried
  6. additionthe dried solution treated with activated charcoal
  7. filtrationfiltered through cellulose
  8. customto crystallize

Sources & evidence

ORD record
ord-b1c0615a3a11477d8398fa1d213160cf
Source dataset
uspto-grants-1985_11
Patent number
US04552888

Reaction notes

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