Water → 2-Chloro-1,3-dimethoxybenzene

HRID 1380173Notes

Reaction equation

HRID 1380173 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.C([Li])CCC.[Cl:16]N1C(=O)CCC1=O.O>COCCOC>[Cl:16][C:4]1[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 90251,3-DimethoxybenzeneHCID 31398ChlorosuccinimideHCID 178418339Butyllithium

Product 1

HCID 130157172-Chloro-1,3-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1,3-dimethoxybenzene (13.8 g) in 1,2-dimethoxyethane (100 ml) is added 2.6M n-butyllithium (40 ml). After 40 minutes, N-chlorosuccinimide (13.5 g) is added and the reaction temperature is maintained below 55° C. by means of an ice-bath. After an additional 45 minutes, the reaction mixture is poured into water and extracted with ether. Evaporation of the organic extract affords an oil which is choromatographed on silica gel (125 g), eluting with 20% ether-hexane. Evaporation of the eluents affords an oil which crystallized on standing. Recrystallization from hexane gives 2-chloro-1,3-dimethoxybenzene, mp 62°-64° C.

Workup

  1. temperaturethe reaction temperature is maintained below 55° C. by means of an ice-bath
  2. waitAfter an additional 45 minutes
  3. extractionextracted with ether
  4. customEvaporation of the
  5. extractionorganic extract
  6. customaffords an oil which
  7. washeluting with 20% ether-hexane
  8. customEvaporation of the eluents
  9. customaffords an oil which
  10. customcrystallized
  11. customRecrystallization from hexane

Sources & evidence

ORD record
ord-7031be316b864f7fa44dcea4c1dbad04
Source dataset
uspto-grants-1986_04
Patent number
US04579981

Reaction notes

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