4-Nitrobenzaldehyde → 4-[3-(4-Methylphenyl)-1-propenyl]nitrobenzene

HRID 1903655Notes

Reaction equation

HRID 1903655 reaction equation
[Br-].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.C([Li])CCC.[N+:35]([C:38]1[CH:45]=[CH:44][C:41]([CH:42]=O)=[CH:40][CH:39]=1)([O-:37])=[O:36]>O1CCCC1.CCCCCC.O>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]=[CH:42][C:41]2[CH:44]=[CH:45][C:38]([N+:35]([O-:37])=[O:36])=[CH:39][CH:40]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 20466351(2-(P-Tolyl)ethyl)triphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 537641644-[3-(4-Methylphenyl)-1-propenyl]nitrobenzeneYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a suspension of [2-(4-methylphenyl)ethyl]triphenyl-phosphonium bromide (55.4 g) in anhydrous tetrahydrofuran (840 ml) kept at -50° C., a 1.5 N solution of n-butyl lithium in hexane (80 ml) was added, and the resultant mixture was stirred for a while. A solution of p-nitrobenzaldehyde (15.1 g) in anhydrous tetrahydrofuran (100 ml) was added thereto. The resulting mixture was allowed to stand at room temperature overnight, diluted with water and extracted with ethyl acetate. The extract was concentrated under reduced pressure and chromatographed on a column with silica gel, followed by eluting with a mixture of hexane and ethyl acetate to give 4-[3-(4-methylphenyl)-1-propenyl]nitrobenzene (21 g). nD24 1.5321.

Workup

  1. customkept at -50° C.
  2. extractionextracted with ethyl acetate
  3. concentrationThe extract was concentrated under reduced pressure
  4. customchromatographed on a column with silica gel
  5. washby eluting with a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-9021908dc47c46efa83876e513d26111
Source dataset
uspto-grants-1984_03
Patent number
US04437880

Reaction notes

Loading…