Dimethylformamide → 8-Methoxy-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde

HRID 497029Notes

Reaction equation

HRID 497029 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10])[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].CN(C=O)C.Br[CH2:25][CH2:26]Br>O>[CH3:12][O:11][C:8]1[C:9]2[O:10][CH2:25][CH2:26][O:1][C:2]=2[CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 775353,4-Dihydroxy-5-methoxybenzaldehyde

Product 1

HCID 6065788-Methoxy-2,3-dihydro-1,4-benzodioxine-6-carbaldehydeYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

In a vial was placed 0.5 g (3.0 mmol) of 3,4-dihydroxy-5-methoxybenzaldehyde, 414 mg (3.0 mmol) of K2CO3, and 3 mL of anhydrous DMF. To this mixture was added, 0.56 g (3.0 mmol) of 1,2-dibromoethane dropwise. The vial was sealed and heated to 100° C. overnight. Water was added to the reaction and the mixture was extracted with diethyl ether. The organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated to give the crude product. The material was purified by silica gel chromatography using 50% ethyl acetate/hexane as the eluent to afford 0.25 g (43%) of the pure aldehyde 10.

Workup

  1. additionTo this mixture was added
  2. customThe vial was sealed
  3. extractionthe mixture was extracted with diethyl ether
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product
  10. customThe material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a4782987aa6047e68ec8565ac771b778
Source dataset
uspto-grants-2005_09
Patent number
US06949544B2

Reaction notes

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