Catechol → 1,2-Dihexyloxybenzene

HRID 1760901Notes

Reaction equation

HRID 1760901 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)O)[OH:2].[C:9]([O-:12])([O-])=O.[K+].[K+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].O>CN(C=O)C>[CH2:16]([O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:12][CH2:9][CH2:7][CH2:8][CH2:1][CH2:3][CH3:5])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 289CatecholHCID 962WaterHCID 81011-BromohexaneHCID 11430Potassium Carbonate

Product 1

HCID 43816021,2-Dihexyloxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

Pyrocatechol (55.1 g; 0.5 mol) is dissolved in DMF (400 ml), and K2CO3 (207.3 g) is added. The mixture is heated to 70° C. 1-Bromohexane (198 g; 1.2 mol) is then added dropwise, and heating is carried out for 15 hours at 80° C. Further DMF (400 ml) and water (1 liter) are subsequently added. Extraction is then carried out with tert-butyl methyl ether (2×500 ml), and the organic phase is washed with water (3×100 ml) and dried over Na2SO4. After filtration, concentration to dryness by evaporation is carried out.

Workup

  1. temperatureheating
  2. extractionExtraction
  3. washthe organic phase is washed with water (3×100 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration, concentration to dryness
  6. customby evaporation

Sources & evidence

ORD record
ord-422fd8590d604940bcd36514af19b257
Source dataset
uspto-grants-2005_01
Patent number
US06846492B2

Reaction notes

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