1,2-Dichloro-4-nitrobenzene → HCID 20393486, compound

HRID 1862796Notes

Reaction equation

HRID 1862796 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1Cl.[CH:12]1([CH2:15][OH:16])[CH2:14][CH2:13]1.[OH-].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[O:16][CH2:15][CH:12]1[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 75644Cyclopropanemethanol

Product 1

HCID 20393486HCID 20393486, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution containing 38.4 g of 3,4-dichloronitrobenzene in 150 ml of DMSO was added 17.3 g of cyclopropylmethanol. This solution was stirred during the dropwise addition of 9.2 g of sodium hydroxide dissolved in 10 ml of water. This addition was exothermic to 45° C. The mixture was stirred and heated to 75°-80° for 18 hours, than poured over ice water and filtered. The filter cake was recrystallized from methanol to yield 27 g (59%) of light tan solid, melting point, 42°-44° C.

Workup

  1. additionThis addition
  2. customwas exothermic to 45° C
  3. temperatureheated to 75°-80° for 18 hours
  4. filtrationfiltered
  5. customThe filter cake was recrystallized from methanol
  6. customto yield 27 g (59%) of light tan solid
  7. custompoint, 42°-44° C.

Sources & evidence

ORD record
ord-5f939b5df184433d8352072a58ef79ec
Source dataset
uspto-grants-1979_09
Patent number
US04166735

Reaction notes

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