Dimethylformamide → 6-Methyl-2H-1,3-benzodioxole-5-carbaldehyde

HRID 1265019Notes

Reaction equation

HRID 1265019 reaction equation
CN([CH:4]=[O:5])C.P(Cl)(Cl)(Cl)=O.[CH2:11]1[O:19][C:18]2[CH:17]=[CH:16][C:15]([CH3:20])=[CH:14][C:13]=2[O:12]1>>[CH3:20][C:15]1[CH:14]=[C:13]2[O:12][CH2:11][O:19][C:18]2=[CH:17][C:16]=1[CH:4]=[O:5]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 815641,3-Benzodioxole, 5-methyl-

Product 1

HCID 31462426-Methyl-2H-1,3-benzodioxole-5-carbaldehydeYield 11%

Conditions

Temperature
0 °C

Procedure

To DMF (6.5 ml, 83 mmoles) at 0° C. was added phosphorus oxychloride (3.9 ml, 42 mmoles). The solution was stirred 15 minutes at 0° C. followed by the addition of 3,4-(methylenedioxy)toluene (1.0 ml, 8.3 mmoles). The solution was heated to 110° C. upon which it became dark brown. 1.5 hours later the thick dark brown mixture was cooled to ambient temperature then added to ice (100 ml), and extracted with ether (100 ml). The organic layer was dried (MgSO4), filtered and concentrated. Flash chromatography (5% EtOAc/hexanes) provided 0.15 g (11%) of the title compound as a colorless oil.

Workup

  1. temperatureThe solution was heated to 110° C. upon which it
  2. temperature1.5 hours later the thick dark brown mixture was cooled to ambient temperature
  3. extractionextracted with ether (100 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-571369fe5aba458d815b5b435a3c9f46
Source dataset
uspto-grants-2003_04
Patent number
US06545014B2

Reaction notes

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