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

HRID 1583749Notes

Reaction equation

HRID 1583749 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-to-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. customat room temperature
  2. extractionThe resulting mixture was extracted with methylene chloride
  3. washthe extract was washed with ice water
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0c7d4b96926d45f790aa7c5cfd98498c
Source dataset
uspto-grants-1985_11
Patent number
US04554283

Reaction notes

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