Dimethylformamide → 2-Benzofurancarboxaldehyde

HRID 2248025Notes

Reaction equation

HRID 2248025 reaction equation
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][O:9][C:4]2=[CH:3][CH:2]=1.CN(C)[CH:12]=[O:13].P(Cl)(Cl)(Cl)=O>>[O:9]1[C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=2[CH:7]=[C:8]1[CH:12]=[O:13]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 9223BenzofuranHCID 24813Phosphorus oxychloride

Product 1

HCID 613412-BenzofurancarboxaldehydeYield 31.5%

Conditions

Temperature
50 °C

Procedure

To a mixture of 2,3-benzofuran (23.63 g, 0.2 mol) and N,N-dimethylformamide (22 g, 0.3 mol) was added phosphorous oxychloride (46 g, 0.3 mol) dropwise. Upon completion of addition, the mixture was stirred for 1 hr, then warmed to 50° C. and kept at that temperature for 60 hrs. It was then poured into ice (250 mL). The resulting aqueous mixture was neutralized to pH6 by the addition of aqu. 2N NaOH and extracted with ether (3×300 mL). The organics were combined, dried with MgSO4 and concentrated. The residue was distilled to afford 9.21 g of 2-benzofurancarboxaldehyde as a pale yellow oil (b.p.=98°-100° C. at 0.6 mm Hg).

Workup

  1. additionUpon completion of addition
  2. waitkept at that temperature for 60 hrs
  3. additionThe resulting aqueous mixture was neutralized to pH6 by the addition of aqu
  4. extraction2N NaOH and extracted with ether (3×300 mL)
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-e26496e0370d45e1872aae1fa08cdb83
Source dataset
uspto-grants-1991_08
Patent number
US05037853

Reaction notes

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