Sodium Carbonate → 3,5-Bis[2-(3,5-di-tert-butylphenyl)ethenyl]benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dibromobenzaldehyde (31.7 g, 120 mmoles), 3,5-di-t-butylstyrene (65.0 g, 301 mmoles), anhydrous sodium carbonate (31.9 g, 301 mmoles), trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]dipalladium (II) (244 mg, 0.26 mmoles, 0.1 mole %), 2,6-di-t-butylcresol (13.3 g, 60 mmoles) and anhydrous N,N-dimethylacetamide (130 mL) was degassed thoroughly whilst stirring under oil-pump vacuum, purging with argon. The reaction mixture was then heated under argon at 130° C. for 26.5 h. After cooling, ether (250 mL) and hydrochloric acid (1.5 M, 150 mL) were added carefully. A suspension remained in the organic layer, which was washed with distilled water (5×125 mL) and evaporated. The combined aqueous layers were extracted with ether (100 mL) and this organic extract was washed with distilled water (4×30 mL) and combined with the main organic fraction. The crude product was triturated thoroughly with cold pet. ether (40-60), filtered and recrystallized from dichloromethane/pet. ether (60-80) to give colourless crystals of 3,5-bis(3′,5′-di-t-butylstyryl)benzaldehyde (44.61 g, 69%), m.p. 217-219° C. (Found: C, 87.7; H, 9.7. C39H50O requires C, 87.6; H, 9.4%); νmax (CHCl3)/cm−1 1698s (C═O), 1596s (C═C) and 964s (C═C—H trans); λmax (CHCl3)/nm 316 (log ε/dm3 mol−1 cm−1 4.65); δH(500 MHz; CDCl3) 1.41 (36H, s, t-Bu), 7.20 and 7.34 (4H, d, J 16, vinyl H), 7.43 (2H, dd, J 2, sp H), 7.44 (4H, d, J 2, sp H), 7.94 (1H, m, cp H), 7.95 (2H, d, J 1.5, cp H) and 10.11 (1H, s, CHO); m/z (APCI+) 535 (M+, 100%).

Provenance & Evidence