Benzyl Chloride → p-(Benzyloxy)phenethyl alcohol

HRID 2380173Notes

Reaction equation

HRID 2380173 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH2:17]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 10393TyrosolHCID 11430Potassium Carbonate

Product 1

HCID 3017260p-(Benzyloxy)phenethyl alcohol

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Procedure

To a flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was added 13.8 grams of 2-(4-hydroxyphenyl)ethanol, 14.5 grams of anhydrous potassium carbonate, 33.0 grams of tetrabutylammonium bromide, 12 mL of benzyl chloride and 200 mL of acetone. The reaction mixture was heated at reflux for 3 days, and then cooled to room temperature and filtered. The filtrate was concentrated in vacuo, diluted with 500 mL of dichloromethane, and washed with 2% aqueous sodium hydroxide and then with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting product was purified by chromatography on silica gel, eluting with dichloromethane, to yield 20.0 grams of the desired product as a white solid.

Workup

  1. customTo a flask equipped with a magnetic stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 3 days
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. additiondiluted with 500 mL of dichloromethane
  8. washwashed with 2% aqueous sodium hydroxide
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe resulting product was purified by chromatography on silica gel
  13. washeluting with dichloromethane

Sources & evidence

ORD record
ord-14c23be8d39e47c79d58654182b26a4d
Source dataset
uspto-grants-1994_11
Patent number
US05366517

Reaction notes

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