Tetrahydrofuran → Maltol

HRID 2082656Notes

Reaction equation

HRID 2082656 reaction equation
[O:1]1CCCC1.ClCl.[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]([OH:15])[CH3:14].BrBr>O>[CH3:14][C:13]1[O:15][CH:12]=[CH:11][C:10](=[O:1])[C:9]=1[OH:8]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24408BromineHCID 24526ChlorineHCID 1072431-(2-Furyl)ethanol

Product 1

HCID 8369Maltol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In a 3-neck round bottom flask equipped with a magnetic stirring bar, a gas inlet tube, a thermometer and an addition funnel was added 50 ml of tetrahydrofuran and 50 ml of water. This solution was then cooled to 0° C. and chlorine (0.10 mole) was added slowly to the reaction flask while 1(2-furyl)-1-ethanol (0.09 mole) was added dropwise. The temperature of the reaction mixture was not allowed to exceed 10° C. Bromine (0.10 mole) was then added and the reaction mixture heated to reflux. Following the isolation procedure of Example 1, a yield of 5.7 g of maltol was obtained.

Workup

  1. customIn a 3-neck round bottom flask equipped with a magnetic stirring bar, a gas inlet tube
  2. additionwas added dropwise
  3. customto exceed 10° C
  4. temperaturethe reaction mixture heated to reflux

Sources & evidence

ORD record
ord-7bd8b3a4d1514b5e847ed27cc692dc42
Source dataset
uspto-grants-1978_04
Patent number
US04082717

Reaction notes

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