3-Nitrobenzaldehyde → HCID 53943132, compound

HRID 1291754Notes

Reaction equation

HRID 1291754 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[N+:6]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)([O-:8])=[O:7]>O1CCCC1>[CH:12]([C:11]1[CH:10]=[C:9]([N+:6]([O-:8])=[O:7])[CH:16]=[CH:15][CH:14]=1)=[CH:4][CH2:3][CH2:2][CH2:1][CH2:15][CH2:16][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 53943132HCID 53943132, compound

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, and a solution of 3-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 57.3 g of 3-(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-ffe1dad6a4ad4a7eb2853737e202cf97
Source dataset
uspto-grants-1998_05
Patent number
US05753649

Reaction notes

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