Hydroquinone → HCID 131729977, compound

HRID 2060578Notes

Reaction equation

HRID 2060578 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[CH:6]([OH:9])([CH3:8])[CH3:7].[C:10]1([CH:17]=[CH:16][C:14]([OH:15])=[CH:13][CH:12]=1)[OH:11].[OH-:18].[Na+]>O>[C:6]1([C:8]2[CH:4]3[O:5][CH:3]3[CH2:1][O:18][CH2:12][CH:10]3[O:11][CH:17]3[C:16]=2[C:14](=[CH:13][CH:7]=1)[OH:15])[OH:9]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 3776IsopropanolHCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide

Product 1

HCID 131729977HCID 131729977, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
79 °C

Procedure

Epichlorohydrin (222 g, 2.4 mol), isopropyl alcohol (120 mL), and hydroquinone (33 g, 0.3 mol) were added to a four-neck 1 L round bottom flask equipped with a condenser, mechanical stirrer, nitrogen source, and an addition funnel containing 28.8 g NaOH in 40 g water. While purging with nitrogen, NaOH solution was added dropwise and the reaction was then heated to 75-83° C. The solution color changed from dark brown to yellow with white solid precipitate after 6 hours. The solution was filtered and the solvents removed to give a viscous yellow liquid, which solidified on cooling and was collected. The product was recrystallized in isopropyl alcohol twice, then distilled under vacuum to give a white solid upon cooling. 1H NMR (CDCl3): δppm 2.7-2.9 (4H), 3.3-3.4 (2H), 3.9-4.2 (4H), 6.9 (4H).

Workup

  1. customequipped with a condenser, mechanical stirrer
  2. customWhile purging with nitrogen, NaOH solution
  3. additionwas added dropwise
  4. customafter 6 hours
  5. filtrationThe solution was filtered
  6. customthe solvents removed
  7. customto give a viscous yellow liquid, which
  8. temperatureon cooling
  9. customwas collected
  10. customThe product was recrystallized in isopropyl alcohol twice
  11. distillationdistilled under vacuum
  12. customto give a white solid
  13. temperatureupon cooling

Sources & evidence

ORD record
ord-6dbdd44388fe473d92cf7243b9603399
Source dataset
uspto-grants-2012_10
Patent number
US08278401B2

Reaction notes

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