3-Nitrobenzaldehyde → 3-Nitrostyrene

HRID 326616Notes

Reaction equation

HRID 326616 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH2:12]([Li])CCC.CCCCCC>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:7]([C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=[CH:10][CH:9]=1)=[CH2:12]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 8058HexaneHCID 178418339Butyllithium

Product 1

HCID 685143-Nitrostyrene

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

Treatment of 3-nitrobenzaldehyde (20 g) with methyltriphenylphosphonium bromide (61.5g) and n-butyllithium in hexane (172 mmol), as described in Example 1a, gave 3-ethenylnitrobenzene (10.3 g), δ (360 MHz, CDCl3), 5.44 and 5.59 (2H, 2d, CH2), 6.75 (1H, dd, CH), 7.49 (1H, t, 5-H), 7.70 (1H, dd, 4-H), 8.09 (1H, dd, 6-H) and 8.24 (1H, d, 2-H).

Sources & evidence

ORD record
ord-55eec336f68f4793a8f9bef4c706144a
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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