2-Nitrobenzaldehyde → HCID 19754698, compound

HRID 1588775Notes

Reaction equation

HRID 1588775 reaction equation
[Br-].[CH:2]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CC(C)([O-])C.[K+].[N+:33]([C:36]1[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=1[CH:38]=O)([O-:35])=[O:34]>C1COCC1>[C:2]1(=[CH:38][C:37]2[CH:40]=[CH:41][CH:42]=[CH:43][C:36]=2[N+:33]([O-:35])=[O:34])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 111012-NitrobenzaldehydeHCID 2724861Cyclohexyl(triphenyl)phosphanium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 19754698HCID 19754698, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of cyclohexyl triphenylphosphonium bromide (16.6 g) in THF (100 mL) at 24° C. was added potassium t-butoxide (4.38 g). The mixture was stirred for 30 min. o-Nitrobenzaldehyde (3.93 g) in THF (50 mL) was added dropwise below 30° C. and stirred for 30 min. The mixture was then partitioned between EtOAc and ice water. The EtOAc layer was washed well with water, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silica gel with 5% EtOAc/hexanes to give 1-(cyclohexylidenemethyl)-2-nitrobenzene.

Workup

  1. additionwas added dropwise below 30° C.
  2. customThe mixture was then partitioned between EtOAc and ice water
  3. washThe EtOAc layer was washed well with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-0d1748c9c17c4d39ab3ceac48294f29e
Source dataset
uspto-grants-1993_06
Patent number
US05223526

Reaction notes

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