Bromine → Maltol

HRID 46440Notes

Reaction equation

HRID 46440 reaction equation
[C:1]([C:4]1[O:5][CH:6]=[CH:7][C:8]=1Cl)(=[O:3])[CH3:2].[BH4-].[Na+].[OH:12]C(C1OC=CC=1Cl)C.BrBr>CO.O>[CH3:8][C:4]1[O:5][CH:6]=[CH:7][C:2](=[O:12])[C:1]=1[OH:3]

Participants

7

Reactant 4

HCID 24408BromineHCID 4311764Sodium borohydrideHCID 20348365HCID 20348365, compoundHCID 22607842HCID 22607842, compound

Product 1

HCID 8369Maltol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

2-Acetyl-3-chloro-furan (1.0 g, 7 mmoles) in 30 ml methanol was cooled to 10° C. and 0.065 g, (1.7 mmoles) of NaBH4 added in one portion. After stirring for 30 minutes at 25° C., the solution was treated with 15 ml of water and cooled to 5° C. To the formed 2-(1-hydroxyethyl)-3-chloro-furan was then added 1.1 g (7 mmoles) of bromine, dropwise and with cooling. After the addition was complete the reaction was heated to 95° C. for 2 hours, distilling off a portion of the methanol. The reaction was then cooled and maltol isolated by the method of Example 1.

Workup

  1. temperaturecooled to 5° C
  2. temperaturedropwise and with cooling
  3. additionAfter the addition
  4. temperaturewas heated to 95° C. for 2 hours
  5. distillationdistilling off a portion of the methanol
  6. temperatureThe reaction was then cooled

Sources & evidence

ORD record
ord-636529bf8c044b80ad25cd39db528472
Source dataset
uspto-grants-1979_11
Patent number
US04173572

Reaction notes

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