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-b95d77541a2447d8ab12cf6e276c3ff1

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06462194B1