Tetrahydrofuran → Maltol

HRID 25905

Reaction equation

HRID 25905 reaction equation
[O:1]1CCCC1.BrBr.[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]([OH:15])[CH3:14]>O>[CH3:14][C:13]1[O:15][CH:12]=[CH:11][C:10](=[O:1])[C:9]=1[OH:8]

Participants

5

Reactant 3

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

Product 1

HCID 8369MaltolYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

To a 4-neck round bottom flask equipped with a thermometer, a condensor and two addition funnels was charged 50 ml of tetrahydrofuran and 50 ml of water and the solution was cooled to 10° C. To this well stirred solution was added together in the two addition funnels bromine (0.20 mole) and 1(2-furyl)-1-ethanol (0.09 mole). The temperature of the reaction was maintained at 15° C. throughout the double addition. The reaction mixture was then heated to 75° C. for 10 hours. Maltol was isolated by the procedure of Example 1 (53% yield).

Workup

  1. customTo a 4-neck round bottom flask equipped with a thermometer
  2. additiona condensor and two addition funnels
  3. temperatureThe temperature of the reaction was maintained at 15° C. throughout the double addition
  4. temperatureThe reaction mixture was then heated to 75° C. for 10 hours

Sources & evidence

ORD record
ord-86108ece6be54748bf031644ae43cd30
Source dataset
uspto-grants-1979_04
Patent number
US04147705

Linked notes

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