Dihydrobenzofuran → 2,3-Dihydrobenzofuran-5-carboxaldehyde

Temperature

0 °C

To a stirred solution of α,α-dichloromethyl methyl ether (2.15 g, 19 mmol, 1.35 eq) in methylene chloride (30 mL) at -40° C. was added successively stannic chloride (1.65 g, 17 mmol, 1.2 eq) and 15 minutes later, a solution of 2,3-dihydrobenzofuran (1.68 g, 14 mmol) in CH2Cl2 (5 mL) maintaining the temperature at or below -35° C. The mixture was warmed to 0° C., stirred 1 hour, then poured into ice-water, and stirred a further 30 minutes. The mixture was diluted with ether, and the phases separated. The organic phase was concentrated in vacuo, and the residue purified by vacuum distillation to yield the title compound (1.25 g, 60%) as a colorless liquid. b.p. 119°-121° C. at 0.3 mm Hg.

1. stirringstirred a further 30 minutes
2. customthe phases separated
3. concentrationThe organic phase was concentrated in vacuo
4. distillationthe residue purified by vacuum distillation

ORD record

ord-a77e34e2ec91434fa697b43c33d45133

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05731434