Benzyl Chloride → 2-(Benzyloxy)-5-(tert-butyl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of compound 2 (614.5 g, 3.33 mol) in DMF (3.5 L) was added K2CO3 (953 g, 6.90 mol) and benzyl chloride (480 g, 3.80 mol). The mixture was heated to 90° C. and left stirring for 3 hours. The suspension was cooled to room temperature, then MTBE (2 L) was added, followed by water (12 L). The mixture was then stirred for 10 minutes and the aqueous layer was separated and extracted with MTBE (2 L×3). The organic layers were combined and washed with water (2 L×2) and brine (1.5 L×1) and concentrated to give compound 3 as a light-yellow solid. 1H NMR (DMSO-d6; 400 MHz) δ 10.42 (s), δ 7.71 (m), δ 7.51 (m), δ 7.43 (m), δ 7.35 (m), δ 7.24 (m), δ 5.27 (s), δ 1.26 (s).

Provenance & Evidence