Water → Maltol

HRID 1164270Notes

Reaction equation

HRID 1164270 reaction equation
[OH2:1].[Br-].[Na+].[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH:9]([OH:11])[CH3:10].ClCl>O1CCCC1>[CH3:10][C:9]1[O:11][CH:8]=[CH:7][C:6](=[O:1])[C:5]=1[OH:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24526Chlorine2×HCID 1072431-(2-Furyl)ethanolHCID 253881Sodium Bromide

Product 1

HCID 8369MaltolYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

In a 3-neck round bottom flask equipped with a stirring bar, a gas inlet tube and an addition funnel was added 20 ml of tetrahydrofuran, 50 ml of water and sodium bromide (0.20 mole). The solution was cooled to a temperature of 0 to 20° C. The addition funnel was charged with a solution of 1(2-furyl)-1-ethanol (0.18 mole) in 20 ml of tetrahydrofuran and this was added dropwise to the rapidly stirred reaction flask while gaseous chlorine (0.40 mole) is added via the gaseous inlet tube. The rate of the alcohol addition was such that a yellow orange color was maintained. The reaction temperature was kept below 20° C. with ice bath cooling. After the alcohol and chlorine had both been added to the reaction flask, the temperature was raised to reflux to distill off the tetrahydrofuran. The isolation procedure of Example 1 was used to isolate 12.47 g of pure maltol (55% yield).

Workup

  1. customIn a 3-neck round bottom flask equipped with a stirring bar, a gas inlet tube and an addition funnel
  2. additionis added via the gaseous inlet tube
  3. temperaturewas maintained
  4. customThe reaction temperature was kept below 20° C. with ice bath
  5. temperaturecooling
  6. additionboth been added to the reaction flask
  7. temperaturethe temperature was raised
  8. temperatureto reflux
  9. distillationto distill off the tetrahydrofuran

Sources & evidence

ORD record
ord-8b0ab203ba2540f9bc4fe8a0e4daf1f7
Source dataset
uspto-grants-1983_01
Patent number
US04368331

Reaction notes

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