Benzyl Chloride → 2,5-Dimethyl-4-(phenylmethoxy)benzenemethanol

HRID 374297Notes

Reaction equation

HRID 374297 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][OH:10])=[C:4]([CH3:11])[CH:3]=1.[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:11][C:4]1[CH:3]=[C:2]([O:1][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]([CH3:8])=[CH:6][C:5]=1[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 109426404-Hydroxymethyl-2,5-dimethylphenol

Product 1

HCID 198096502,5-Dimethyl-4-(phenylmethoxy)benzenemethanolYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 18.0 g (118 mmol) of 4-hydroxy-2,5-dimethyl-benzenemethanol (Example H), 14.9 g (118 mmol) of benzyl chloride and 18.0 g (1.1×118 mmol) of anhydrous potassium carbonate in 300 mL of acetonitrile is stirred at reflux for 18 hours overnight. The reaction flask and inorganic residue are washed with fresh acetonitrile and the solvent is removed on a rotary evaporator. A diethyl ether solution of the residue is washed with 2×50 mL of 2N potassium hydroxide solution, brine, dried (magnesium sulfate) and evaporated leaving 28.3 g of a pale yellow viscous residue. Distillation through a short path apparatus affords the title compound; mp 58°-59° C.

Workup

  1. temperatureat reflux for 18 hours overnight
  2. washThe reaction flask and inorganic residue are washed with fresh acetonitrile
  3. customthe solvent is removed on a rotary evaporator
  4. washA diethyl ether solution of the residue is washed with 2×50 mL of 2N potassium hydroxide solution, brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-c9cd4979606142c3a7e69d6daac3a432
Source dataset
uspto-grants-1992_11
Patent number
US05166398

Reaction notes

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