Water → 1-Bromo-4-(hexyloxy)-2,5-dimethylbenzene

HRID 2120042Notes

Reaction equation

HRID 2120042 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[Br:16]Br.O>ClCCCl>[Br:16][C:6]1[C:5]([CH3:8])=[CH:4][C:3]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 23437455HCID 23437455, compound

Product 1

HCID 698829561-Bromo-4-(hexyloxy)-2,5-dimethylbenzeneYield 97.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In 250 g of ethanol were dissolved 250 g (2.05 mol) of 2,5-dimethylphenol (or p-xylenol), 90 g (2.25 mol) of sodium hydroxide and 371 g (2.25 mol) of n-hexyl bromide. The solution was heated for 2 hours in an oil bath at 80° C. Water, 500 g, was added to the reaction mixture, from which an oily matter was separated. Vacuum distillation of the oily matter yielded 384 g of 2,5-dimethyl-1-n-hexyloxy-benzene. Next, 129 g (0.625 mol) of 2,5-dimethyl-1-n-hexyloxybenzene was dissolved in 625 g of 1,2-dichloroethane. To the solution kept in an ice bath, 100 g (0.625 mol) of bromine was added dropwise at a temperature below 5C. At the end of dropwise addition, 500 g of water was added. The organic layer was separated therefrom and washed with 300 g of an aqueous solution of 5 wt % sodium hydrogen carbonate. The organic layer was concentrated to remove the solvent, leaving an oily matter. Vacuum distillation (boiling point 114-124° C./0.5 Torr) of the oily matter yielded 174 g of 4-bromo-2,5-dimethyl-n-hexyloxybenzene.

Workup

  1. customTo the solution kept in an ice bath
  2. additionwas added
  3. customThe organic layer was separated
  4. washwashed with 300 g of an aqueous solution of 5 wt % sodium hydrogen carbonate
  5. concentrationThe organic layer was concentrated
  6. customto remove the solvent
  7. customleaving an oily matter
  8. distillationVacuum distillation (boiling point 114-124° C./0.5 Torr) of the oily matter

Sources & evidence

ORD record
ord-87067e6671624ae39df531542c9913e6
Source dataset
uspto-grants-2004_02
Patent number
US06689530B2

Reaction notes

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