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

HRID 2218455Notes

Reaction equation

HRID 2218455 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]>O.[Pd]>[CH2:11]([OH:12])[C@H:9]([OH:10])[C@H:7]1[O:8][C:2](=[O:1])[C@@H:3]([OH:4])[C@H:5]1[OH:6]

Participants

4

Reactant 1

HCID 54670067L-Ascorbic Acid

Product 1

HCID 439373L-Gulonic acid, gamma-lactoneYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a solution of L-ascorbic acid (83.9 g, 0.477 mole) in water (600 mL) was added Pd/C (10%, 8.3 g). The mixture was subjected to hydrogenation in a Parr hydrogenator at 48 psi, 18° C. for 62 hrs. The reaction mixture was filtered and the filtrate was concentrated in vacuo to afford L-gulonic γ-lactone (81.0 g, 96%) as an off-white solid, after drying at 50° C. in a vacuum oven for 18 hrs: m.p. 182-184° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3bec0a9074a7469882ddec6e4742b9e4
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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