Dimethyl Sulfate → 1,3-Dichloro-4-methoxy-2-nitrobenzene

HRID 1902865Notes

Reaction equation

HRID 1902865 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[CH:5]=[CH:4][C:3]=1[OH:12].[OH-].[Na+].S(OC)(O[CH3:19])(=O)=O>C(Cl)Cl.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[CH:5]=[CH:4][C:3]=1[O:12][CH3:19]

Participants

7

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 205139322,4-Dichloro-3-nitrophenol

Product 1

HCID 205138861,3-Dichloro-4-methoxy-2-nitrobenzene

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 155.4 g of 2,4-dichloro-3-nitrophenol in 2 l of methylene chloride is treated with 16.9 g of benzyltrimethylammonium chloride. There is added thereto a solution of 44.8 g of sodium hydroxide in 1.8 l of water and, while stirring vigorously, 143 ml of dimethyl sulfate. After 1 hour, the organic phase is separated, washed with water, dried and evaporated in vacuo. There is obtained 2,4-dichloro-3-nitroanisole of melting point 97°-99° (hexane).

Workup

  1. additionThere is added
  2. customthe organic phase is separated
  3. washwashed with water
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-b4b0d6bc19a14b90a43aaa7fe88e31f1
Source dataset
uspto-grants-1982_12
Patent number
US04366160

Reaction notes

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