Benzaldehyde → 1-methoxy-4-(2-nitroethyl)benzene

HRID 849146Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C(=O)C1C=CC=CC=1.NC1C=CC=CC=1N>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][N+:9]([O-:11])=[O:10])=[CH:12][CH:13]=1

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 7243O-Phenylenediamine

HCID 2298434-Methoxy-beta-nitrostyrene

Product 1

HCID 4878921-methoxy-4-(2-nitroethyl)benzeneYield 93%

Procedure

Example 227 A) 4-Methoxy-β-nitrostyrene (25.0 g, 0.15 mole) was reacted with benzaldehyde (19.1 g, 0.18 mole) and 1,2-diaminobenzene (19.8 g, 0.18 mole) according to the procedure of Chikashita et. al. (Synth. Commun. 1985, 15 (6), 527) to yield methoxy-4-(2-nitroethyl) benzene (25.0 g, 93%) as a yellow oil.

Sources & evidence

ORD record: ord-f6603cee6dab49c9bd9e97318741ce51
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011028

Reaction notes

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