4-Methylbenzyl chloride → Salicylic Acid

HRID 358756Notes

Reaction equation

HRID 358756 reaction equation
CC([C:10]1[CH:18]=[C:14]([C:15]([OH:17])=[O:16])[C:13]([OH:19])=[CH:12][CH:11]=1)(C)C1C=CC=CC=1.CC1C=CC(CCl)=CC=1>[Cl-].[Zn+2].[Cl-].[N+](C)([O-])=O>[C:15]([OH:17])(=[O:16])[C:14]1[C:13](=[CH:12][CH:11]=[CH:10][CH:18]=1)[OH:19]

Participants

5

Reactant 2

HCID 77224-Methylbenzyl chlorideHCID 707669Benzoic acid, 2-hydroxy-5-(1-methyl-1-phenylethyl)-

Product 1

HCID 338Salicylic Acid

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6375NitromethaneSolvent

Procedure

A glass-made reactor was charged with 5.1 g (0.02 mole) of 5-(α, α-dimethylbenzyl)salicylic acid, 50 ml of nitromethane, and as a catalyst, 1.4 g of anhydrous zinc chloride. The resultant mixture was maintained at 95° C. under stirring. At the same temperature, 22.5 g (0.16 mole) of p-methylbenzyl chloride was added dropwise over 10 hours to conduct a reaction. After completion of the dropwise addition, the reaction mixture was aged for 2 hours at the same temperature to complete the reaction. The weight average molecular weight of the thus-obtained resin was 2400.

Workup

  1. customa reaction
  2. additionAfter completion of the dropwise addition
  3. customthe reaction

Sources & evidence

ORD record
ord-36648ea43bfd4d90911751dc4b2eaba5
Source dataset
uspto-grants-1991_03
Patent number
US04997874

Reaction notes

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