L-Ascorbic Acid → L-Gulonic acid, gamma-lactone

HRID 514605

Reaction equation

HRID 514605 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].[H][H]>O.[Pd]>[C:2]1(=[O:1])[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C@H:5]([OH:6])[C@@H:3]1[OH:4]

Participants

5

Reactant 2

HCID 54670067L-Ascorbic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 439373L-Gulonic acid, gamma-lactoneYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A solution of L-ascorbic acid (23.1 g, 0.13 mol) in 170 ml of water was hydrogenated using 10% Pd/C (2.2 g) in a Parr hydrogenator at 50° C. and 50 psi hydrogen pressure for 24 hours. The catalyst was removed by filtration and the water removed in vacuo to afford 23.2 g (0.13 mol, 99%) of a white crystalline solid. Upon recrystallization from methanol-ethyl acetate, 22.0 g of the desired product was obtained. 1H NMR (DMSO): δ 5.80 (d, 1H). 5.30 (d, 1H), 4.95 (d, 1H), 4.65 (t, 1H), 4.45 (m, 1H), 4.23-4.15 (m, 2H), 3.75 (m, 1H), 3.48 (m, 2H).

Workup

  1. customat 50° C.
  2. customThe catalyst was removed by filtration
  3. customthe water removed in vacuo

Sources & evidence

ORD record
ord-7b7ac7707828493da999617514bc239e
Source dataset
uspto-grants-2015_08
Patent number
US09107956B2

Linked notes

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