2,4-Dimethylbenzyl chloride → Salicylic Acid

HRID 358757

Reaction equation

HRID 358757 reaction equation
C([C:5]1[CH:13]=[C:12](C2C=CC=CC=2)[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]=1[OH:20])(C)(C)C.CC1C=C(C)C=CC=1CCl>[Cl-].[Zn+2].[Cl-].C(O)(=O)C>[CH:12]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([OH:20])=[CH:5][CH:13]=1

Participants

5

Reactant 2

HCID 699892,4-Dimethylbenzyl chlorideHCID 19033707HCID 19033707, compound

Product 1

HCID 338Salicylic Acid

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

A glass-made reactor was charged with 5.4 g (0.02 mole) of 3-tert-butyl-5-phenylsalicylic acid, 30 ml of glacial acetic acid, and as a catalyst, 1.4 g of anhydrous zinc chloride. The resultant mixture was heated under stirring and maintained under reflux. Then, 12.4 g (0.08 mole) of 2,4-dimethylbenzyl chloride was added dropwise over 6 hours to conduct a reaction. After completion of the dropwise addition, the reaction mixture was aged for 2 hours under reflux to complete the reaction. The weight average molecular weight of the thus-obtained resin was 1680.

Workup

  1. temperaturemaintained
  2. temperatureunder reflux
  3. customa reaction
  4. additionAfter completion of the dropwise addition
  5. temperatureunder reflux
  6. customthe reaction

Sources & evidence

ORD record
ord-f700f97ee1c842859990c4c6a8f417a6
Source dataset
uspto-grants-1991_03
Patent number
US04997874

Linked notes

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