Dimethyl Sulfoxide → 1-(allyloxy)-2-nitrobenzene

HRID 482957Notes

Reaction equation

HRID 482957 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])([O-:5])=[O:4].Cl[CH2:14][CH:15]=[CH2:16].CS(C)=O>O>[CH2:16]([O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[N+:3]([O-:5])=[O:4])[CH:15]=[CH2:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 69472-NitrophenolHCID 7850Allyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 112753631-(allyloxy)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 64 g of sodium hydroxide in 75 ml of water was added drop-by-drop (over 15 minutes) to a stirred mixture of 209.6 g of 2-nitrophenol, 115.5 g of 3-chloropropene and 500 ml of dimethyl sulfoxide (DMSO), at room temperature. The mixture was stirred at 85°-90° C. for 18 hours and then mixed with 3 liters of water. The resulting mixture was extracted with methylene chloride, the extract was washed with ice water, dried (MgSO4) and the solvent was evaporated, to give 1-(2-propen-1-yloxy)-2-nitrobenzene (1A), as an amber syrup.

Workup

  1. extractionThe resulting mixture was extracted with methylene chloride
  2. washthe extract was washed with ice water
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-20175829047f41e5aa450d1f3e69a1ac
Source dataset
uspto-grants-1986_03
Patent number
US04577011

Reaction notes

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