Hydroquinone → 1,4-Bis(2-ethylhexyloxy)benzene

HRID 1050491Notes

Reaction equation

HRID 1050491 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].Br[CH2:10][CH:11]([CH2:16][CH3:17])[CH2:12][CH2:13][CH2:14][CH3:15].[OH-].[K+].[CH2:20]([CH:22]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:23]O)[CH3:21]>O>[CH2:16]([CH:11]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][O:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH2:23][CH:22]([CH2:20][CH3:21])[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:4][CH:3]=1)[CH3:17]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 77202-EthylhexanolHCID 14797Potassium Hydroxide2×HCID 868042-Ethylhexyl bromide2×

Product 1

HCID 35799201,4-Bis(2-ethylhexyloxy)benzeneYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydroquinone (37.9 g, 0.344 mol) is suspended in IMS (310 ml) and 1-bromo-2-ethylhexane (132.7 g, 0.687 mol) is added. A solution of KOH (49.9 g, 0.89 mol) in IMS (250 ml) is added slowly over 1 minute. The mixture is heated at reflux whilst monitoring reaction progress by HPLC. After 16 hours, further 1-bromo-2-ethylhexane (53.1 g, 0.27 mol) and solid KOH (20.0 g, 0.36 mol) are added then heated for 2 hours at reflux. The reaction mixture is allowed to cool, is poured into water (1.5 L) and extracted with toluene (500 ml). The organic layer is dried over MgSO4 then evaporated to yield a pale yellow oil. The oil is flashed through silica gel, eluting with 50/50 dichloromethane/hexane to give two product fractions. The initial fraction (35.3 g) co-eluted with 2-ethylhexan-1-ol by-product. The second fraction is evaporated to give pure 1,4-bis(2-ethylhexyloxy)benzene as a pale yellow oil (48.4 g, 42%). The initial fraction is further purified by bulb to bulb distillation to give further pure 1,4-bis(2-ethylhexyloxy)benzene as a pale yellow oil (25.3 g, 22%).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux
  3. customreaction progress by HPLC
  4. temperaturethen heated for 2 hours
  5. temperatureat reflux
  6. temperatureto cool
  7. extractionextracted with toluene (500 ml)
  8. dry with materialThe organic layer is dried over MgSO4
  9. customthen evaporated
  10. customto yield a pale yellow oil
  11. washeluting with 50/50 dichloromethane/hexane
  12. customto give two product fractions
  13. customThe second fraction is evaporated

Sources & evidence

ORD record
ord-7b7fdf442a9348928eafde2e57799031
Source dataset
uspto-grants-2016_07
Patent number
US09383621B2

Reaction notes

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