1,1-Dichloroethane → 1-Bromo-4-(2,2-dimethoxyethoxy)-2,3-dimethylbenzene

HRID 703298Notes

Reaction equation

HRID 703298 reaction equation
[Br:1]Br.ClC(Cl)C.[CH3:7][O:8][CH:9]([O:20][CH3:21])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[CH3:19].[OH-].[Na+]>CO>[Br:1][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH:9]([O:20][CH3:21])[O:8][CH3:7])=[C:13]([CH3:19])[C:14]=1[CH3:18]

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 14798Sodium HydroxideHCID 24408BromineHCID 4198790HCID 4198790, compound

Product 1

HCID 147515551-Bromo-4-(2,2-dimethoxyethoxy)-2,3-dimethylbenzeneYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Bromine (140 g) was added dropwise to a 760 ml of dichloroethane solution containing 180 g of 1-(2,2-dimethoxyethoxy)-2,3-dimethylbenzene while stirring and cooling (ice bath) and maintaining the temperature of the reaction mixture not exceeding 10° C. After stirring for 30 minutes after completion of the addition, the reaction mixture was condensed under reduced pressure (a temperature of 40° C. or lower). The condensate was added dropwise in a solution comprising 37 g of sodium hydroxide dissolved in 185 g of methanol while stirring. Stirring was continued for one hour after completion of the addition, methanol was removed under reduced pressure, and 30 ml of dichloroethane and 570 ml of water were added to the residue and then the mixture was separated with each other. The organic layer was condensed under reduced pressure, a resulting brownish oil was distilled under reduced pressure to give 228 g of 1-bromo-4-(2,2-dimethoxyethoxy)-2,3-dimethylbenzene. Boiling point: 128° to 131° C./0.5 mmHg; Melting point: 40° to 41° C.; and Yield: 92%.

Workup

  1. temperaturecooling (ice bath)
  2. temperaturemaintaining the temperature of the reaction mixture not
  3. customexceeding 10° C
  4. stirringAfter stirring for 30 minutes
  5. additionafter completion of the addition
  6. customcondensed under reduced pressure (a temperature of 40° C.
  7. additionThe condensate was added dropwise in a solution
  8. stirringwhile stirring
  9. stirringStirring
  10. customwas removed under reduced pressure, and 30 ml of dichloroethane and 570 ml of water
  11. additionwere added to the residue
  12. customthe mixture was separated with each other
  13. customcondensed under reduced pressure
  14. distillationa resulting brownish oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-485dc46038054992ba411f5314dcf14a
Source dataset
uspto-grants-1991_01
Patent number
US04982008

Reaction notes

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