4-Chloro-3-methylphenol → HCID 13655351, compound

HRID 745269Notes

Reaction equation

HRID 745269 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[Br:10][CH2:11][CH2:12][CH2:13]Br.[OH-].[Na+]>O>[Br:10][CH2:11][CH2:12][CH2:13][O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:9])[CH:4]=1

Participants

5

Reactant 3

HCID 17324-Chloro-3-methylphenolHCID 80011,3-DibromopropaneHCID 14798Sodium Hydroxide

Product 1

HCID 13655351HCID 13655351, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred and refluxing mixture of 122 parts of 4-chloro-3-methylphenol, 214.1 parts of 1,3-dibromopropane and 850 parts of water added dropwise, during a one hour-period, a solution of 34 parts of sodium hydroxide in 213 parts of water. Upon completion, stirring at reflux is continued overnight. The reaction mixture is cooled to room temperature and the product is extracted with 765 parts of benzene. The extract is washed with a sodium hydroxide solution 10%, dried, filtered and evaporated. The residue is distilled twice, yielding 114 parts of 4-(3-bromopropoxy)-1-chloro-2-methylbenzene; bp. 119° C. at 0.6 mm. pressure.

Workup

  1. temperaturerefluxing
  2. additionadded dropwise, during a one hour-period
  3. stirringUpon completion, stirring
  4. temperatureat reflux
  5. extractionthe product is extracted with 765 parts of benzene
  6. washThe extract is washed with a sodium hydroxide solution 10%
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. distillationThe residue is distilled twice

Sources & evidence

ORD record
ord-dadb938e1f3c4b3db792d882e133bcf0
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

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