Hydrochloric Acid → Salicylic Acid

HRID 358758Notes

Reaction equation

HRID 358758 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=CC=CC=2)[C:5](CC2C=CC=CC=2)=[CH:4][C:3]=1[C:19]([OH:21])=[O:20].[Cl-].[Al+3].[Cl-].[Cl-].C(Br)C1C=CC=CC=1.Cl>ClCCCl>[C:19]([OH:21])(=[O:20])[C:3]1[C:2](=[CH:11][CH:6]=[CH:5][CH:4]=1)[OH:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 6451240Aluminum(III) ChlorideHCID 19880852HCID 19880852, compound

Product 1

HCID 338Salicylic AcidYield 296.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Charged were 5.50 g (0.02 mole) of 1-hydroxy-2-carboxy-4-benzylnaphthalene, 50 ml of 1,2-dichloroethane, and as a catalyst, 2.7 g of anhydrous aluminum chloride. The resultant mixture was maintained at 70° C. under stirring. Then, 5.2 g (0.03 mole) of benzyl bromide was added dropwise over 6 hours to conduct a reaction. After completion of the dropwise addition, the reaction mixture was aged for 2 hours at the same temperature and then poured into dilute hydrochloric acid. The resultant mixture was allowed to separate into layers. The lower organic layer was concentrated to obtain 8.2 g of a reddish brown resin. The weight average molecular weight of the resin was 720.

Workup

  1. additionCharged
  2. customa reaction
  3. additionAfter completion of the dropwise addition
  4. customto separate into layers
  5. concentrationThe lower organic layer was concentrated

Sources & evidence

ORD record
ord-e75b69f0d1a14a52abb0c9de7fcbb003
Source dataset
uspto-grants-1991_03
Patent number
US04997874

Reaction notes

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