Chlorine → Maltol

HRID 1903327Notes

Reaction equation

HRID 1903327 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:8])[CH3:7].Cl[O-:10].[Na+].ClCl>O1CCCC1.O>[CH3:7][C:6]1[O:8][CH:5]=[CH:4][C:3](=[O:10])[C:2]=1[OH:1]

Participants

6

Reactant 3

HCID 24526ChlorineHCID 1072431-(2-Furyl)ethanolHCID 23665760Sodium Hypochlorite

Product 1

HCID 8369Maltol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1(2-furyl)-1-ethanol (0.05 mole) in 15 ml of tetrahydrofuran and 15 ml of water at 5° C. is added 21.7 ml of 2.8 M sodium hypochlorite solution. Chlorine (0.05 mole) is added to the reaction flask via a gas inlet tube maintaining the reaction temperature below 5° C. The reaction mixture is then heated to reflux and the tetrahydrofuran removed by distillation. Heating is continued for an additional hour. The reaction mixture is cooled and maltol is isolated by the procedure described in Example 1.

Workup

  1. temperaturemaintaining the reaction temperature below 5° C
  2. temperatureThe reaction mixture is then heated
  3. temperatureto reflux
  4. customthe tetrahydrofuran removed by distillation
  5. temperatureHeating
  6. waitis continued for an additional hour
  7. temperatureThe reaction mixture is cooled

Sources & evidence

ORD record
ord-5dd32531f3e54a12bb769316c31940f2
Source dataset
uspto-grants-1984_03
Patent number
US04435584

Reaction notes

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