Ammonia → 4-Ethoxy-2-methyl-1-nitrobenzene

HRID 2174509Notes

Reaction equation

HRID 2174509 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH2:18](OS(OCC)(=O)=O)[CH3:19].N>CC(=O)CC>[CH2:18]([O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=1)[CH3:19]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 174123-Methyl-4-nitrophenol

Product 1

HCID 115645664-Ethoxy-2-methyl-1-nitrobenzeneYield 106.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

3-Methyl-4-nitrophenol 403 (500 mg, 3.0 mmol) was dissolved in 2-butanone (10 mL). Potassium carbonate (903 mg, 6.5 mmol) was added to the solution followed by diethylsulfate (0.45 mL, 3.2 mmol). The reaction mixture was heated at 70° C. for 2 h. Upon completion, the mixture was cooled to rt and aqueous ammonia (30%, 1 mL) was added and stirred for 18 h at rt. The reaction mixture was filtered and washed with 2-butanone (30 mL). The filtrate was collected and evaporated in vacuo to yield a white solid (580 mg, 97%). mp 50-52° C. (lit.53 mp 51° C.). TLC Rf 0.65 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3) δ 8.11-8.09 (d, 1H, J=8.88 Hz), 6.82-6.78 (m, 2H), 4.14-4.10 (q, 2H, J=6.96 Hz), 2.65 (s, 3H), 1.48-1.46 (t, 3H, J=6.95 Hz). 13C NMR (150 MHz, CDCl3) δ 162.5, 142.0, 137.1, 127.6, 117.9, 112.2, 64.2, 21.8, 14.6.

Workup

  1. temperatureUpon completion, the mixture was cooled to rt
  2. filtrationThe reaction mixture was filtered
  3. washwashed with 2-butanone (30 mL)
  4. customThe filtrate was collected
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-655dc5a6679a44318e5aae71a77144d0
Source dataset
uspto-grants-2015_06
Patent number
US09061994B1

Reaction notes

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