2,5-Dimethylphenol → HCID 23437455, compound

HRID 2120041Notes

Reaction equation

HRID 2120041 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[C:10]1(O)(C)[CH:15]=[CH:14][C:13](C)=[CH:12][CH2:11]1.[OH-].[Na+].C(Br)CCCCC>C(O)C.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH2:14][CH2:15][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 72672,5-DimethylphenolHCID 81011-BromohexaneHCID 14798Sodium HydroxideHCID 67419026HCID 67419026, compound

Product 1

HCID 23437455HCID 23437455, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

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. customwas separated
  2. distillationVacuum distillation of the oily matter

Sources & evidence

ORD record
ord-74869d71993943f389136507d8d44cf3
Source dataset
uspto-grants-2004_02
Patent number
US06689530B2

Reaction notes

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