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

HRID 1727139Notes

Reaction equation

HRID 1727139 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)benzene

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.

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

Sources & evidence

ORD record
ord-0f1198f3c4c74e01817a58f8d922f0b5
Source dataset
uspto-grants-2009_02
Patent number
US07495016B2

Reaction notes

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