Nitromethane → 1-Benzyloxy-2-cyclopentyloxy-4-(2-nitrovinyl)benzene

HRID 1819336Notes

Reaction equation

HRID 1819336 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[O:17][CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][N+:24]([O-:26])=[O:25]>CC(O)=O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[CH:23][N+:24]([O-:26])=[O:25])=[CH:11][C:10]=1[O:17][CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6375NitromethaneHCID 211878994-Benzyloxy-3-cyclopentyloxybenzaldehyde

Product 1

HCID 688282011-Benzyloxy-2-cyclopentyloxy-4-(2-nitrovinyl)benzeneYield 44.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-benzyloxy-3-cyclopentyloxybenzaldehyde (6.3 g, 21.3 mmol) in AcOH (13 mL) and CH3NO2 (5.8 mL, 106.5 mmol) was created. NH4OAc (3.3 g, 42.5 mmol) was added and the mixture was heated under reflux for 2 h. After cooling to r.t., the mixture was extracted with CH2Cl2. The organic layer separated and washed with water, sat. NaHCO3, and sat. NaCl, and dried over Na2SO4. Concentration under reduced pressure and purification by column chromatography on silica gel (CH2Cl2/hexane) gave 3.2 g of yellow solids. Yield: 44%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. extractionthe mixture was extracted with CH2Cl2
  4. customThe organic layer separated
  5. washwashed with water, sat. NaHCO3, and sat. NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration
  8. customunder reduced pressure and purification by column chromatography on silica gel (CH2Cl2/hexane)

Sources & evidence

ORD record
ord-3b0f91f59c664fa297eb485deade29c0
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

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