Nitromethane → (E)-2-(1-Admantyl)-1-isopropoxy-4-(2-nitrovinyl)benzene

Reaction equation

[C:1]12([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=3[O:19][CH:20]([CH3:22])[CH3:21])[CH:14]=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CC([O-])=O.[NH4+].[CH3:28][N+:29]([O-:31])=[O:30]>>[C:1]12([C:11]3[CH:12]=[C:13](/[CH:14]=[CH:28]/[N+:29]([O-:31])=[O:30])[CH:16]=[CH:17][C:18]=3[O:19][CH:20]([CH3:22])[CH3:21])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

Reactant 3

HCID 6375Nitromethane

HCID 517165Ammonium Acetate

HCID 871266563-(1-Admantyl)-4-isopropoxybenzaldehyde

Product 1

HCID 66727011(E)-2-(1-Admantyl)-1-isopropoxy-4-(2-nitrovinyl)benzeneYield 88%

Procedure

To a stirred solution of 3-(1-admantyl)-4-isopropoxybenzaldehyde (0.24 g, 0.8 mmol) in CH3NO2 (5 mL) was added CH3CO2NH4 (0.125 g, 1.6 mmol) and the mixture was stirred for 3 h at reflux. The solvent was evaporated to dryness and the residue was diluted to 50 ml with EtOAc and washed with 1M HCl and H2O. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title product (0.275 g; 88%) as yellow solid. 1H-NMR (CDCl3) 1.41 (d, 6H, J=6 Hz); 1.7-1.76 (m, 6H); 2.08-2.12 (m, 9H); 4.68-4.74 (m, 1H); 6.85 (d, 1H, J=8.45 Hz); 7.33-7.38 (m, 2H); 7.51 (d, 1H, J=13.53 Hz); 7.97 (d, 1H, J=13.54 Hz).