Resorcinol → Benzyl 3-hydroxyphenyl ether

HRID 2181179Notes

Reaction equation

HRID 2181179 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>O>[C:10]1([CH2:9][O:2][C:1]2[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 138048Benzyl 3-hydroxyphenyl etherYield 27.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

36.6 g (332.40 mmol) of resorcinol and 42 g (331.78 mmol) of benzyl chloride are refluxed overnight in 250 ml of dry Me2CO in the presence of 46.6 g of K2CO3, with stirring. The mixture is cooled, filtered and evaporated. The residue obtained is diluted in 500 ml of water and extracted with ethanol. The organic layer is washed with 10% aqueous NaOH and extracted with ethanol. The red oil obtained is distilled with the aid of a bulb tube distillation apparatus to give 18 g of m-PhCH2OC6H4OH, b.p.15 240-245° C. (lit. b.p.11 202-210° C.). A solution of 3.3 g (16.5 mmol) of m-PhCH2OC6H4OH in 50 ml of DMF is treated with 0.8 g (16.5 mmol) of sodium hydride and the mixture is stirred for 15 minutes. After the addition of 13.75 ml (16.5 mmol) of epichlorohydrin, the mixture is stirred at 60° C. for one hour until alkylation is complete. The excess reagent and the solvent are evaporated off under reduced pressure and the residue is partitioned between the following two phases: ethyl acetate and water. The organic phase yields the epoxide, which is used without further purification.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue obtained
  5. extractionextracted with ethanol
  6. washThe organic layer is washed with 10% aqueous NaOH
  7. extractionextracted with ethanol
  8. customThe red oil obtained
  9. distillationis distilled with the aid of a bulb tube
  10. distillationdistillation apparatus

Sources & evidence

ORD record
ord-f5aaf8debb164e96a3e566559d54bc29
Source dataset
uspto-grants-2005_05
Patent number
US06890955B2

Reaction notes

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