Ethanol → HCID 86724048, compound

HRID 1753758Notes

Reaction equation

HRID 1753758 reaction equation
[CH3:1][CH2:2][O-:3].[Na+].CCO.Cl[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=1>O>[CH2:2]([O:3][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=1)[CH3:1]

Participants

5

Reactant 3

HCID 702EthanolHCID 5977304-(Chloromethyl)-2-nitrotolueneHCID 2723922Sodium ethoxide

Product 1

HCID 86724048HCID 86724048, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of NaOEt in dry EtOH (45 mL, 114.90 mmol) under inert atmosphere was added 4-chloromethyl-1-methyl-2-nitro-benzene (7.0 g, 38.30 mmol). The reaction mixture was stirred at room temperature for 16 hours. Water was added and ethanol 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 I-g as brown oil in 96% yield. 1H NMR (300 MHz, CDCl3) δ 7.95 (s, 1H), 7.48 (d, J=7.8 Hz, 1H), 7.31 (d, J=7.9 Hz, 1H), 4.52 (s, 2H), 3.56 (q, J=7.0 Hz, 2H), 2.57 (d, J=10.1 Hz, 3H), 1.26 (t, J=7.0 Hz, 3H).

Workup

  1. customethanol 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 I-g as brown oil in 96% yield

Sources & evidence

ORD record
ord-568da4cba44c4a1eb1ff1021caf4d6cc
Source dataset
uspto-grants-2015_10
Patent number
US09168245B2

Reaction notes

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