Dimethylformamide → 3,3-Dimethyl-2,3-dihydrobenzofuran-5-carbaldehyde

HRID 444071Notes

Reaction equation

HRID 444071 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH3:11][C:12]1([CH3:21])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH2:13]1.C([O-])(=O)C.[Na+]>O>[CH3:11][C:12]1([CH3:21])[C:16]2[CH:17]=[C:18]([CH:8]=[O:9])[CH:19]=[CH:20][C:15]=2[O:14][CH2:13]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 111593943,3-Dimethyl-2,3-dihydro-1-benzofuran

Product 1

HCID 205361803,3-Dimethyl-2,3-dihydrobenzofuran-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (30.6 g, 0.2 mole) was added dropwise to a mixture of dimethyl formamide (14.6 g, 0.2 mole) and 2,3-dihydro-3,3-dimethyl benzofuran (14.8 g, 0.1 mole) over half an hour. The temperature rose to 55° C. during addition. The temperature was then raised to 100° C. and maintained for 1 hour prior to addition to a hot solution of sodium acetate (75 g) in water (75 ml). After cooling, the organic layer was separated, dried and distilled yielding 5.6 g unchanged starting material bp 35°-40° C. at 0.1 mm and 5.2 g aldehyde bp 85° C. at 0.1 mm. The product contained a little 2,2-dimethyl isomer from the previous stage.

Workup

  1. additionThe temperature rose to 55° C. during addition
  2. temperaturemaintained for 1 hour
  3. temperatureAfter cooling
  4. customthe organic layer was separated
  5. customdried
  6. distillationdistilled
  7. customyielding 5.6 g

Sources & evidence

ORD record
ord-5590edc81bd24d21a07dff3f24fa9bc9
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

Loading…