Bromine → Maltol
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
Product 1
Reagents, catalysts & solvents 2
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
- temperaturecooled to 5° C
- temperaturedropwise and with cooling
- additionAfter the addition
- temperaturewas heated to 95° C. for 2 hours
- distillationdistilling off a portion of the methanol
- temperatureThe reaction was then cooled
Sources & evidence
- ORD record
- ord-e2f20df9988649a4a39903d9d15687a1
- Source dataset
- uspto-grants-1980_03
- Patent number
- US04191693
Reaction notes
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