Dimethylformamide → 2,3-Dihydro-1,4-benzodioxine-5-carbaldehyde

HRID 842722Notes

Reaction equation

HRID 842722 reaction equation
[OH:1][C:2]1[C:9](O)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].CN(C)[CH:13]=[O:14].[C:16](=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C>[CH2:16]1[CH2:13][O:14][C:9]2[C:2](=[C:3]([CH:6]=[CH:7][CH:8]=2)[CH:4]=[O:5])[O:1]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 27950332,3-Dihydro-1,4-benzodioxine-5-carbaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a 100 ml round bottom flask fitted with a nitrogen gas inlet, condenser, and a magnetic stirring bar were placed 2,3-dihydroxybenzaldehyde (4.00 g, 29.0 mmol), 70 ml anhydrous dimethylformamide, and cesium carbonate (14.15 g, 43.5 mmol). The mixture was heated to 110° and stirred for 2.5 hours. The reaction was allowed to cool to room temperature and ethyl acetate was added. This solution was washed four times with brine, dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed (0-10% ethyl acetate/hexanes to give 4.07 g of subtitled product (86%) which was used directly in the next step.

Workup

  1. customInto a 100 ml round bottom flask fitted with a nitrogen gas inlet, condenser, and a magnetic stirring bar
  2. temperatureThe mixture was heated to 110°
  3. washThis solution was washed four times with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed (0-10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-cf6ac40a45c74b8bb81e35fa212820c3
Source dataset
uspto-grants-2002_04
Patent number
US06376505B1

Reaction notes

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