Hydroquinone → 4-(2-Phenoxyethoxy)phenol

HRID 1249652Notes

Reaction equation

HRID 1249652 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].Br[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[K+]>O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 14797Potassium HydroxideHCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 202239004-(2-Phenoxyethoxy)phenolYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100 ml of water were added 40 g of hydroquinone, 20 g of β-bromophenetole and 6 g of potassium hydroxide and the mixture was subjected to reaction at 80° C. for about 2 hours. The solid precipitated was filtered and washed with warm water. The unreacted materials were extracted with alkali for removal. The remaining insoluble solids were removed by filtration and the filtrate was neutralized with hydrochloric acid. The solid precipited was filtered, washed with water and recrystallized from ethyl alcohol, giving 1-(4-hydroxyphenoxy)-2-phenoxy ethane in a yield of 85%. M.p. 156° C.

Workup

  1. customthe mixture was subjected to reaction at 80° C. for about 2 hours
  2. customThe solid precipitated
  3. filtrationwas filtered
  4. washwashed with warm water
  5. extractionThe unreacted materials were extracted with
  6. customalkali for removal
  7. customThe remaining insoluble solids were removed by filtration
  8. filtrationThe solid precipited was filtered
  9. washwashed with water
  10. customrecrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-67459e8500044bd68a1439e84cfd80d7
Source dataset
uspto-grants-1986_12
Patent number
US04633277

Reaction notes

Loading…