Ethanol → 3-O-Ethylascorbic acid

HRID 1175199Notes

Reaction equation

HRID 1175199 reaction equation
[CH2:1]([O:3][C:4]1[C@@H:9]([C@H:10]([C:12](=C(C)C)[OH:13])[OH:11])[O:8][C:6](=[O:7])[C:5]=1[OH:17])[CH3:2].C(O)C>O.Cl>[CH2:1]([O:3][C:4]1[C@@H:9]([C@H:10]([CH2:12][OH:13])[OH:11])[O:8][C:6](=[O:7])[C:5]=1[OH:17])[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 66915691HCID 66915691, compound

Product 1

HCID 1507363-O-Ethylascorbic acidYield 84.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

12.4 g of the 3-O-ethyl-isopropylidene ascorbic acid obtained in Example 1 was dissolved in 100 ml of distilled water, to which 10 ml of 2N hydrochloric acid solution was added. The mixture was reacted at 60° C. for 2 hours and concentrated under reduced pressure to give an adhesive liquid product. Ethanol was added to the prepared liquid product, which was then concentrated to give crude crystalline 3-ethyl-ascorbic acid. The crude crystalline 3-ethyl-ascorbic acid was re-crystallized in ethylacetate/ethanol (8:2) to give 8.6 g of white crystalline 3-O-ethyl-ascorbic acid (yield: 84.3%).

Workup

  1. additionwas added
  2. customThe mixture was reacted at 60° C. for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. customto give an adhesive liquid product
  5. concentrationwas then concentrated
  6. customto give crude crystalline 3-ethyl-ascorbic acid
  7. customThe crude crystalline 3-ethyl-ascorbic acid was re-crystallized in ethylacetate/ethanol (8:2)

Sources & evidence

ORD record
ord-1dbce865394346f88324c9844697df1c
Source dataset
uspto-grants-2010_11
Patent number
US07838690B2

Reaction notes

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