Ethanol → Ethyl 3-nitro-1-naphthoate
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].O=S(Cl)Cl.[CH3:21][CH2:22]O>>[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([O:16][CH2:21][CH3:22])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2]Participants
4
Procedure
To a solution of 3-nitronaphthalene-1-carboxylic acid (4.34 g, 20 mmol) in EtOH (50 mL) was added SOCl2 (3.70 mL, 30 mmol) at 0° C. The mixture was heated at reflux for 2 h and then concentrated. The residue was recrystallized from EtOH to yield ethyl 3-nitronaphthalene-1-carboxylate (4.2 g). 1H NMR (300 MHz, DMSO-d6): δ 9.16 (s, 1H), 8.77 (d, J=8.7 Hz, 1H), 8.62 (s, 1H), 8.34 (d, J=8.1 Hz, 1H), 7.87 (t, J=7.2 Hz, 1H), 7.75 (t, J=7.2 Hz, 1H), 4.43 (q, J=7.2 Hz, 2H), 1.38 (t, J=7.2 Hz, 3H).
Workup
- temperature