Hexane → 1-(2-Propenyloxy)-5-chloro-4-methyl-2-nitrobenzene

HRID 465031Notes

Reaction equation

HRID 465031 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=1[CH3:8].[CH3:13][CH2:14][CH2:15]CCC>CS(C)=O>[CH2:15]([O:12][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([CH3:8])=[CH:6][C:5]=1[N+:9]([O-:11])=[O:10])[CH:14]=[CH2:13]

Participants

4

Reactant 2

HCID 8058HexaneHCID 135603035-Chloro-4-methyl-2-nitrophenol

Product 1

HCID 202618201-(2-Propenyloxy)-5-chloro-4-methyl-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 37.5 g of 4B in 200 ml of dimethyl sulfoxide (DMSO) was added drop-by-drop over 30 minutes to a stirred solution of 4.8 g of freshly hexane-washed sodium hydride in 200 ml of DMSO, the temperature being held at 30° C. Then 26.6 3-bromopropene was added drop-by-drop over 10 minutes, and the mixture was stirred at 70° C. for 5 hours. The mixture was mixed with 1 liter of cold water and the resulting mixture was extracted with methylene chloride. The extract was washed with water, dried (MgSO4) and the solvent was evaporated, to give 1-(2-propenyloxy)-5-chloro-4-methyl-2-nitrobenzene (7A), as brown solid, m.p.: not determined.

Workup

  1. washwashed sodium hydride in 200 ml of DMSO
  2. custombeing held at 30° C
  3. additionThen 26.6 3-bromopropene was added drop-by-drop over 10 minutes
  4. additionThe mixture was mixed with 1 liter of cold water
  5. extractionthe resulting mixture was extracted with methylene chloride
  6. washThe extract was washed with water
  7. dry with materialdried (MgSO4)
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-94f07cab2ce94e019909050d8129d302
Source dataset
uspto-grants-1985_10
Patent number
US04550121

Reaction notes

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