Acetone → 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

HRID 571037Notes

Reaction equation

HRID 571037 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][OH:16])[O:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:20]>>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([C:15]([OH:20])=[O:16])[O:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 180AcetoneHCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Product 1

HCID 64807825-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

Procedure

To a solution of 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one (93.4 g, 401 mmol) in 2.6 L of acetone was added 400 mL of Jone's reagent (2.45 M) at 0° C. The reaction was warmed to room temperature, and the mixture was stirred overnight. The solid was removed by filtration, and the filtrate was concentrated. The concentrated residue was poured into water. The resulting white solid was collected and washed with water and dried to obtain 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid. 1H NMR δ (400 MHz, d6-DMSO): 8.34 (s, 1H), 7.42-7.33 (m, 5H), 6.91(s, 1H), 4.95 (s, 2H).

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. additionThe concentrated residue was poured into water
  4. customThe resulting white solid was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-358e0fb89b924fb9aec236d3ae38e72b
Source dataset
uspto-grants-2015_05
Patent number
US09024032B2

Reaction notes

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