Sodium Hydroxide → HCID 15023592, compound

Participants

Reaction Steps

Aqueous 1.0 M NaOH (20 mL) was added to a solution of (E)-ethyl 3-(3,4-bis(difluoromethoxy)phenyl)-2-butenoate (0.36 g, 1.1 mmol) in EtOH (20 mL). The solution was stirred at rt for 16 h and then concentrated under reduced pressure to remove the EtOH. The aqueous phase was acidified with 1 M HCl and extracted with EtOAc, washed with water, brine, dried and concentrated. The crude product was recrystallised from EtOH/water to afford (E)-3-(3,4-dimethoxyphenyl)-2-butenoic acid (0.28 g, 85%) as a colourless crystalline solid; mp 73-74° C.; δH (500 MHz, CDCl3) 2.60 (d, J=1.5 Hz, 3H, CH3), 6.15 (q, J=1.5 Hz, 1H, C═CH), 6.55 (t, J=73 Hz, 2H, OCHF2), 7.28 (d, J5,6=8.0 Hz, 1H, H5), 7.36-7.38 (m, 2H, H2, H6); δC (125 MHz, CDCl3) 18.2, 115.6 (t, J=262 Hz), 115.7 (t, J=262 Hz), 117.2, 120.9, 122.1, 124.7, 140.6, 142.1, 143.1, 155.7, 170.1; νmax 1042, 1254, 1621, 1692, 2926 cm−1.

Provenance & Evidence