Hydrochloric Acid → 3-Phenylbenzaldehyde

To a solution of 22.84 g (95.0 mmol) of 3-bromobiphenyl in 280 ml of dry tetrahydrofuran was added 61 ml (99.8 mmol) of n-butyllithium (1.64 mol/liter, n-hexane solution) at −70 ° C. under an atmosphere of nitrogen. The mixture was stirred at the same temperature for 1 hour, and to this was added dropwise 36.55 g (0.50 mol) of N,N-dimethylformamide. The resultant mixture was stirred overnight, while being slowly warmed to room temperature. To the reaction solution was added 400 ml of about 5% aqueous hydrochloric acid, and the mixture was stirred for 2 hours at room temperature. The mixture was extracted with tert-butyl methyl ether, and the organic layer was washed with an about 5% aqueous solution of sodium bicarbonate and water, then dried and concentrated. The residue was subjected to silica gel column chromatography (eluted with n-hexane, then n-hexane:ethyl acetate=15:1) to obtain 13.95 g (76.56 mmol) of 3-phenylbenzaldehyde.

1. stirringthe mixture was stirred for 2 hours at room temperature
2. extractionThe mixture was extracted with tert-butyl methyl ether
3. washthe organic layer was washed with an about 5% aqueous solution of sodium bicarbonate and water
4. customdried
5. concentrationconcentrated
6. washeluted with n-hexane

ORD record

ord-2d2a7058ff0f4fb7bcb6afd9abe78588

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06489487B1