Mesitylene → 2-Allyl-3,5-dimethylphenol

HRID 277671Notes

Reaction equation

HRID 277671 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 1500 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-cd9a9faced0144879f1ba811fca71bcb
Source dataset
uspto-grants-2002_03
Patent number
US06358887B1

Reaction notes

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