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

HRID 710449Notes

Reaction equation

HRID 710449 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

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 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).

Workup

  1. temperatureat reflux
  2. customThe solvent was evaporated to dryness
  3. additionthe residue was diluted to 50 ml with EtOAc
  4. washwashed with 1M HCl and H2O
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-16d1f5f7402a4179bb71c6074516d24b
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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