Mesitylene → 2-Allyl-3,5-dimethylphenol

HRID 352349Notes

Reaction equation

HRID 352349 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:9]CC=C)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:13]1(C)[CH:18]=C(C)C=C(C)[CH:14]=1>>[CH3:8][C:6]1[C:5]([CH2:18][CH:13]=[CH2:14])=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

3

Reactant 2

HCID 7947MesityleneHCID 257959Allyl 3,5-dimethylphenyl ether

Product 1

HCID 2596542-Allyl-3,5-dimethylphenolYield 74%

Procedure

837 g of allyl 3,5-dimethylphenyl ether (B) were dissolved in 1 500 ml of mesitylene, and the solution was refluxed for two days. The solvent was removed in vacuo and the residue was taken up in tert-butyl methyl ether. The mixture was extracted repeatedly using sodium hydroxide solution, and the aqueous phases were combined and acidified with hydrochloric acid. The product which separates out was taken up in tert-butyl methyl ether, and the mixture was dried over magnesium sulphate, concentrated and distilled. A total of 619 g (74% of theory) of 3,5-dimethyl-2-(2-propen-1-yl)-phenol of a boiling point of 145° C. at 30 mbar and a melting point of 51° C. were obtained.

Workup

  1. temperaturethe solution was refluxed for two days
  2. customThe solvent was removed in vacuo
  3. extractionThe mixture was extracted repeatedly using sodium hydroxide solution
  4. dry with materialthe mixture was dried over magnesium sulphate
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-ec53ee13bf2b4e0e9b4494ce75da357a
Source dataset
uspto-grants-2004_06
Patent number
US06746990B2

Reaction notes

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