4-Nitrobenzaldehyde → 4-(1-Decenyl)nitrobenzene

HRID 234060Notes

Reaction equation

HRID 234060 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[N+:6]([C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)([O-:8])=[O:7]>O1CCCC1>[CH:13]([C:12]1[CH:15]=[CH:16][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][CH:11]=1)=[CH:4][CH2:3][CH2:2][CH2:1][CH2:11][CH2:10][CH2:9][CH2:16][CH3:15]

Participants

4

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 542173234-(1-Decenyl)nitrobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

phosphonium salt (141 g) obtained from n-nonyl bromide (115 ml) and triphenylphosphine (78.5 g) was dissolved in dry tetrahydrofuran (500 ml) and thereto was dropwise added n-butyl lithium (372 ml, 1.6M hexane solution) over not less than 1 hour at 0° C. After the dropwise addition, the reaction mixture was stirred at said temperature for 30 minutes and at room temperature for 1 hour. A solution of 4-nitrobenzaldehyde (45.3 g) in tetrahydrofuran (150 ml) was dropwise added thereto at 0° C. over 1 hour. The reaction mixture was stirred at room temperature for 10 hours and filtered. The residue was washed with ether. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (hexane/ethyl acetate=100:1) to give 70.9 g of 4-(1-decenyl)nitrobenzene (cis/trans=7:3).

Workup

  1. customover not less than 1 hour
  2. customat 0° C
  3. additionAfter the dropwise addition
  4. customfor 30 minutes
  5. waitat 0° C. over 1 hour
  6. stirringThe reaction mixture was stirred at room temperature for 10 hours
  7. filtrationfiltered
  8. washThe residue was washed with ether
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. custompurified by silica gel column chromatography (hexane/ethyl acetate=100:1)

Sources & evidence

ORD record
ord-6900b5cd24ff4969b6ebb49ed763416d
Source dataset
uspto-grants-1997_01
Patent number
US05593988

Reaction notes

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