1-Bromooctane → 1-(Octyloxy)-4-(2,4,4-trimethylpentan-2-yl)benzene

HRID 620706Notes

Reaction equation

HRID 620706 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CN(C)C=O>[CH2:23]([O:15][C:12]1[CH:11]=[CH:10][C:9]([C:1]([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:2])[CH3:3])=[CH:14][CH:13]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 88144-Tert-octylphenolHCID 11430Potassium Carbonate

Product 1

HCID 212440051-(Octyloxy)-4-(2,4,4-trimethylpentan-2-yl)benzeneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To 700 ml of N,N-dimethylformamide were added 206 g of 4-t-octylphenol and 207 g of anhydrous potassium carbonate and the mixture was stirred at 50° C. To the mixture was added dropwise 251 g of 1-bromooctane and thereafter the mixture was stirred for 7 hours at 65° to 80° C. Then, after removing insoluble matter by filtration, water was added to the filtrate thus obtained and the product was extracted with ethyl acetate. The organic solvent layer was collected, washed with a saturated aqueous sodium chloride solution, dried on anhydrous magnesium sulfate, and concentrated under reduced pressure. The oily material thus obtained was distilled under reduced pressure (169°-172° C./0.05-0.06 mmHg) to provide 257 g (81% in yield) of 1-octyloxy-4-t-octylbenzene (Compound A).

Workup

  1. stirringthe mixture was stirred for 7 hours at 65° to 80° C
  2. customThen, after removing insoluble matter
  3. filtrationby filtration, water
  4. additionwas added to the filtrate
  5. customthus obtained
  6. extractionthe product was extracted with ethyl acetate
  7. customThe organic solvent layer was collected
  8. washwashed with a saturated aqueous sodium chloride solution
  9. dry with materialdried on anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe oily material thus obtained
  12. distillationwas distilled under reduced pressure (169°-172° C./0.05-0.06 mmHg)

Sources & evidence

ORD record
ord-b3baf37056c242aab44d43951e06d2e4
Source dataset
uspto-grants-1989_04
Patent number
US04822730

Reaction notes

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