Toluene → HCID 22641248, compound

HRID 2415408Notes

Reaction equation

HRID 2415408 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[CH3:10][CH:11]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:12][CH2:13]Br.[OH-].[Na+].C1(C)C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:10][CH:11]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:12][CH2:13][O:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 1140TolueneHCID 72672,5-DimethylphenolHCID 14798Sodium HydroxideHCID 1379141-Bromo-3,7-dimethyloctane

Product 1

HCID 22641248HCID 22641248, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
95 °C

Procedure

Into a 500 ml four-necked flask was placed 36.7 g (0.3 mol) of 2,5-dimethylphenol, then, 73.0 g (0.33 mol) of 3,7-dimethyloctyl bromide was added, further, 150 g of water and 2.0 g (6.2 mmol) of tetrabutylammonium bromide were charged into the flask, and sufficient nitrogen purge was conducted by bubbling nitrogen through the mixture while stirring. Into this mixed solution was added an aqueous solution of sodium hydroxide (a solution prepared by dissolving 14.4 g (0.36 mol) of sodium hydroxide in 22 g of water) dropwise over 10 minutes while stirring. The mixture was heated to 95° C. and reacted for 30 minutes. Then, the mixture was kept at 100° C. and stirred for 4 hours to complete the reaction. The mixture was cooled to room temperature, and 200 ml of toluene was added before liquid separation. The intended substance was extracted into the organic layer which was washed with 200 ml of a 5% sodium hydroxide aqueous solution. The organic layer was dried over sodium sulfate, then, the solvent was distilled off by an evaporator. The intended 1-(3,7-dimethyloctyloxy)-2,5-dimethylbenzene was obtained from the condensed solution by distillation isolation (101 to 108° C./0.01 mmHg). The yield amount was 54.8 g (0.21 mol) and the yield was 70%.

Workup

  1. customInto a 500 ml four-necked flask was placed
  2. custompurge
  3. customby bubbling nitrogen through the mixture
  4. additionInto this mixed solution was added an aqueous solution of sodium hydroxide (a solution
  5. customprepared
  6. stirringwhile stirring
  7. customreacted for 30 minutes
  8. customwas kept at 100° C.
  9. stirringstirred for 4 hours
  10. customthe reaction
  11. temperatureThe mixture was cooled to room temperature
  12. extractionThe intended substance was extracted into the organic layer which
  13. washwas washed with 200 ml of a 5% sodium hydroxide aqueous solution
  14. dry with materialThe organic layer was dried over sodium sulfate
  15. distillationthe solvent was distilled off by an evaporator

Sources & evidence

ORD record
ord-e8c47552833542f7b55f53907c8857b0
Source dataset
uspto-grants-2004_11
Patent number
US06818733B2

Reaction notes

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