Hydroquinone → 4-(2,3-Epoxy-1-propoxy)-phenol

HRID 1156517Notes

Reaction equation

HRID 1156517 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[CH2:9]([CH:11]1[O:13][CH2:12]1)Cl.[OH-].[Na+]>O>[O:13]1[CH2:12][CH:11]1[CH2:9][O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide

Product 1

HCID 128749844-(2,3-Epoxy-1-propoxy)-phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To an ice-cooled solution of 55 g. (0.5 mole) of hydroquinone and 46 g. (0.5 mole) of epichlorohydrin in 900 ml. of water was added an ice-cooled solution of 20 g. (0.5 mole) of sodium hydroxide in 900 ml. of water. The mixture was allowed to stand at 0° C. for 3 days. After washing with ether, the solution was added to 72 g. of sodium hydroxide in 4 l. of water and stored at 10° C. for 3 hours. The solution was saturated with ammonium carbonate and extracted with chloroform. After drying (Na2SO4) and concentrating the chloroform, the residual oil was predominantly 4-(2,3-epoxy-1-propoxy)phenol (23%) which was used in later steps without further purification.

Workup

  1. temperaturecooled solution of 20 g
  2. washAfter washing with ether
  3. additionthe solution was added to 72 g
  4. waitof water and stored at 10° C. for 3 hours
  5. extractionextracted with chloroform
  6. dry with materialAfter drying (Na2SO4)
  7. concentrationconcentrating the chloroform
  8. customwas used in later steps without further purification

Sources & evidence

ORD record
ord-1195d02014c9414fb35cd32af529f7eb
Source dataset
uspto-grants-1982_06
Patent number
US04336261

Reaction notes

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