Salicylic Acid → 4-Hydroxy-o-toluic acid

HRID 543281Notes

Reaction equation

HRID 543281 reaction equation
O[C:2]1[CH:10]=C[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:11](Cl)(=[O:13])[CH3:12]>CO>[OH:13][C:11]1[CH:10]=[CH:2][C:3]([C:4]([OH:6])=[O:5])=[C:7]([CH3:8])[CH:12]=1

Participants

4

Reactant 2

HCID 338Salicylic AcidHCID 6367Acetyl chloride2×

Product 1

HCID 684754-Hydroxy-o-toluic acidYield 67.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

50 g (0.36 mole) of hydroxy-benzoic acid are dissolved in methanol in a 1 liter capacity Erlenmeyer. The mixture is cooled to a temperature of about 5° C. Thereafter, 70 ml (1 mole) of acetyl chlorine are added drop by drop and the mixture is left to return to ambient temperature. A magnetic stirring is carried out over a period of about ten hours. The methanol is then flushed out under vacuum, in the same way as the hydrochloric acid that is formed and the remaining acetyl chloride. 55 g of a solid brown product are recovered. At this step, the yield of the reaction is 99%. A recrystallization in ethanol produces 37 g of pure product, the melting point of which is 123° C. The overall yield of the reaction is 67%.

Workup

  1. waitthe mixture is left
  2. customto return to ambient temperature
  3. waitis carried out over a period of about ten hours
  4. customThe methanol is then flushed out under vacuum, in the same way as the hydrochloric acid that
  5. customis formed
  6. custom55 g of a solid brown product are recovered
  7. customA recrystallization in ethanol

Sources & evidence

ORD record
ord-ef7cbb6fd7bc4624aab4171a10f593fd
Source dataset
uspto-grants-1987_04
Patent number
US04661576

Reaction notes

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