Water → HCID 86724049, compound

HRID 1753759Notes

Reaction equation

HRID 1753759 reaction equation
[CH3:1][O-:2].[Na+].Cl[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1.O>CO>[CH3:1][O:2][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5977304-(Chloromethyl)-2-nitrotolueneHCID 10942334Sodium Methoxide

Product 1

HCID 86724049HCID 86724049, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of NaOMe (1.6 g, 29.63 mmol) in dry MeOH (40 mL) under inert atmosphere was added 4-chloromethyl-1-methyl-2-nitro-benzene (5.0 g, 26.94 mmol). The reaction mixture was stirred at room temperature for 16 h. Water was added and EtOH was removed under reduced pressure. The crude product was extracted with DCM (2 times) and the organic layer was washed with water, then with a saturated solution of NaCl, dried over MgSO4 and concentrated to give intermediate II-l as yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.94 (s, 1H), 7.47 (d, J=7.8 Hz, 1H), 7.32 (d, J=7.8 Hz, 1H), 4.48 (s, 2H), 3.41 (s, 3H), 2.58 (s, 3H).

Workup

  1. customEtOH was removed under reduced pressure
  2. extractionThe crude product was extracted with DCM (2 times)
  3. washthe organic layer was washed with water
  4. dry with materialwith a saturated solution of NaCl, dried over MgSO4
  5. concentrationconcentrated
  6. customto give intermediate II-l as yellow oil

Sources & evidence

ORD record
ord-bebc4ef5b6c64b7dbab0926ed0f9b138
Source dataset
uspto-grants-2015_10
Patent number
US09168245B2

Reaction notes

Loading…