Hydrochloric Acid → Salicylic Acid

HRID 358755Notes

Reaction equation

HRID 358755 reaction equation
CC1C=CC(C[C:7]2[CH:15]=[C:14](CC3C=CC(C)=CC=3)[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[C:8]=2[OH:24])=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)C1C=CC=CC=1.Cl>C(OC(C)C)(C)C>[C:10]([OH:12])(=[O:11])[C:9]1[C:8](=[CH:7][CH:15]=[CH:14][CH:13]=1)[OH:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 198808262-Hydroxy-3,5-bis[(4-methylphenyl)methyl]benzoic acid

Product 1

HCID 338Salicylic AcidYield 434.4%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

A glass-made reactor was charged with 6.9 g (0.02 mole) of 3,5-di(4-methylbenzyl)salicylic acid, 50 ml of isopropyl ether and as a catalyst, 2.7 g of anhydrous aluminum chloride. The resultant mixture was maintained at 50° C. under stirring. At the same temperature, 7.6 g (0.06 mole) of benzyl chloride was added dropwise over 8 hours to conduct a reaction. After completion of the dropwise addition, the reaction mixture was aged for 2 hours at the same temperature and was then poured into a dilute aqueous solution of hydrochloric acid. The resultant mixture was allowed to separate into layers. The solvent was then distilled out to obtain 12.0 g of a reddish brown resin. The weight average molecular weight of the thus-obtained resin was 1250, while its softening point was 65° C.

Workup

  1. customa reaction
  2. additionAfter completion of the dropwise addition
  3. customto separate into layers
  4. distillationThe solvent was then distilled out

Sources & evidence

ORD record
ord-55832250ff6641e3a936fa1bcedf4f60
Source dataset
uspto-grants-1991_03
Patent number
US04997874

Reaction notes

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