Water → 1,3-Benzodioxole-5-carboxaldehyde, 6-methoxy-

HRID 1857567Notes

Reaction equation

HRID 1857567 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[CH:9]=1.O.CN([CH:21]=[O:22])C>>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[O:16][CH2:15][O:14][C:11]2=[CH:12][C:13]=1[CH:21]=[O:22]

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 5924531,3-Benzodioxole, 5-methoxy-

Product 1

HCID 6018611,3-Benzodioxole-5-carboxaldehyde, 6-methoxy-

Conditions

Temperature
60 °C

Procedure

To a solution of phosphorous oxychloride (3.00 mL, 0.033 mol) in DMF (10 mL) was added a solution of 1-methoxy-3,4-methylenedioxybenzene (2.00 g, 0.013 mol) in DMF (2 mL) at 0° C. After stirring at 60° C. for 18 h the mixture was cooled to 0° C. and then poured into water (500 mL). The precipitate was filtered and dried. The title compound was collected as a yellow solid (2.20 g, 92%): 1H NMR (250 MHz, CDCl3) δ 10.22 (s, 1H), 7.20 (s, 1H), 6.52 (s, 1H), 5.98 (s, 2H), 3.85 (s, 3H); mp: 110°l C.

Workup

  1. temperaturewas cooled to 0° C.
  2. filtrationThe precipitate was filtered
  3. customdried
  4. customThe title compound was collected as a yellow solid (2.20 g, 92%)

Sources & evidence

ORD record
ord-121a1c257a7343bbb18bea68263f4f2d
Source dataset
uspto-grants-2000_11
Patent number
US06147111

Reaction notes

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