Benzyl Chloride → alpha-(p-Benzyloxyphenyl)-p-cresol

HRID 1580253Notes

Reaction equation

HRID 1580253 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:8][CH:9]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 12111Bis(4-hydroxyphenyl)methaneHCID 24758Sodium hydride

Product 1

HCID 18942409alpha-(p-Benzyloxyphenyl)-p-cresol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 3.36 g of sodium hydride (in mineral oil) in 50 ml of dimethylformamide is added dropwise at room temperature a solution of 15 g bis-(p-hydroxyphenyl)-methane in 50 ml dimethylformamide. The resulting solution is stirred at room temperature for one hour. Ten grams of benzyl chloride is added dropwise and the stirring is continued at room temperature overnight. After evaporation of the solvent under reduced pressure, the residue is treated with 100 ml of water and extracted twice with diethyl ether. The combined ether extracts are combined, dried over anhydrous magnesium sulfate, evaporated to dryness, and the resulting oil dissolved in hot ethanol. Bis-p-(benzyloxy)phenyl-methane (m.p. 109.5°-110°C) crystallizes upon cooling and is collected by filtration. The mother liquors are evaporated to dryness and the crystalline mono-addition product is obtained by chromatography on silica gel with chloroform. After separation, the mono-benzyl ether is recrystallized from isopropyl ether, m.p. 95°-96°C.

Workup

  1. waitthe stirring is continued at room temperature overnight
  2. customAfter evaporation of the solvent under reduced pressure
  3. additionthe residue is treated with 100 ml of water
  4. extractionextracted twice with diethyl ether
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. dissolutionthe resulting oil dissolved in hot ethanol
  8. customBis-p-(benzyloxy)phenyl-methane (m.p. 109.5°-110°C) crystallizes
  9. temperatureupon cooling
  10. filtrationis collected by filtration
  11. customThe mother liquors are evaporated to dryness
  12. customthe crystalline mono-addition product is obtained by chromatography on silica gel with chloroform
  13. customAfter separation
  14. customthe mono-benzyl ether is recrystallized from isopropyl ether, m.p. 95°-96°C.

Sources & evidence

ORD record
ord-ef1c2be5af7e441bb28a1fc0b6878a76
Source dataset
uspto-grants-1976_01
Patent number
US03932481

Reaction notes

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