Acetone → 1-(allyloxy)-2-nitrobenzene

HRID 1041142Notes

Reaction equation

HRID 1041142 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[CH3:11][C:12]([CH3:14])=O.ICC=C.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:14]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH:12]=[CH2:11]

Participants

6

Reactant 4

HCID 180AcetoneHCID 69472-NitrophenolHCID 11166Allyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 112753631-(allyloxy)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-nitrophenol (5.2 g, 0.037 mol) in acetone (100 mL, 1 mol) at 0° C. was added 3-iodo-1-propene (3.8 mL, 0.041 mol) and potassium carbonate (5.7 g, 0.041 mol). The reaction mixture was stirred for 1 h at 0° C. then warmed to room temperature overnight. The reaction mixture was worked up by diluting the reaction with water and washing with dichloromethane. The organic phase was washed with a 10% HCl solution, water and brine then dried over magnesium sulfate, filtered and concentrated in vacuo to a greenish-brown oil. Purification of the reaction mixture was accomplished using ISCO chromatography on silica gel (350 g column) using hexane-ethyl acetate (0-100%). The major fractions were combined and concentrated in vacuo to give product, 1-allyloxy-2-nitrobenzene, as a light yellow-green oil (5.4 g, 81%). 1H NMR (CDCl3, 400 MHz) δ 7.83 (d, 1H, J=8.09 Hz), 7.51 (t, 1H, J=8.08 Hz), 7.08 (d, 1H, J=8.33 Hz), 7.03 (t, 1H, J=8.08 Hz), 6.04 (m, 1H), 5.49 (d, 1H, J=17.2 Hz), 5.32 (d, 1H, J=10.6 Hz), 4.69 (d, 2H, J=5.05 Hz).

Workup

  1. temperaturethen warmed to room temperature overnight
  2. additionby diluting
  3. washwashing with dichloromethane
  4. washThe organic phase was washed with a 10% HCl solution, water and brine
  5. dry with materialthen dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a greenish-brown oil
  8. customPurification of the reaction mixture
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0945f28569a4220ae3a7c2ffe7e1192
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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