2-Propenoic acid, 3-(4-formylphenyl)- → HCID 54422591, compound

Participants

Reaction Steps

A solution of NaBH4 (0.53 g, 14 mmol) in THF/H2O (4:1) (12 ml) was added dropwise to an ice-cold stirred solution of 4-formylcinnamic acid (2.47 g, 14 mmol) in THF (25 ml), and the mixture was stirred at room temperature for 3 h. The reaction was quenched by adding 4N HCl (20 ml), and the THF was removed by a rotary evaporator. The solid residue was treated with H2O (20 ml), and extracted with EtOAc (4×50 ml). The EtOAc extracts were washed with H2O (50 ml) and brine (50 ml), and dried. The crude product was recrystallized from EtOAc to afford pure 4-hydroxymethylcinnamic acid 124 (1.3 g, 52% yield) as yellow solid. 1H NMR (300 MHz, CD3OD): δ4.62 (s, 2H), 6.45 (d, J=16.2 Hz, 1H), 7.38 (d, J=8.1 Hz, 2H), 7.56 (d, J=8.1 Hz, 2H), 7.65 (d, J=16.2 Hz, 1H); 13C NMR (75 MHz, CD3OD): δ63.53, 117.81, 127.17, 128.08, 133.58, 144.25, 144.92, 169.22; MS (ESI): m/z 177 (M−1).

Provenance & Evidence