Formic Acid → Maltol

HRID 46442Notes

Reaction equation

HRID 46442 reaction equation
O[CH:2]([C:4]1([O:13]C)[C:8]([O:9]C)=[CH:7][CH:6]([O:11]C)O1)[CH3:3].C(O)=O.O>CO>[CH3:3][C:2]1[O:11][CH:6]=[CH:7][C:8](=[O:9])[C:4]=1[OH:13]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 20348360HCID 20348360, compound

Product 1

HCID 8369MaltolYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2(1-hydroxy ethyl)-2,3,5-trimethoxy-2,5-dihydrofuran (2.82 g, 0.015 moles) in 2 ml methanol was added to 15 ml of formic acid over 5 minutes. To the well stirred solution was then added 20 ml of water and the reaction heated to reflux for 1 hour. After cooling, the reaction was extracted with chloroform and the chloroform concentrated to yield 1.5 g maltol, which was recrystallized from methanol to yield the pure white solid, m.p. 159°-160° C. Hydrochloric acid, hydrobromic acid, p-toluene sulfonic acid and acidic ion exchange resins can be used in place of formic acid in this Example.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. extractionthe reaction was extracted with chloroform
  5. concentrationthe chloroform concentrated

Sources & evidence

ORD record
ord-8f92a1e20f6843a6bc6bdda1639b2b65
Source dataset
uspto-grants-1979_11
Patent number
US04173572

Reaction notes

Loading…