Hydrochloric Acid → 3-Acetoxy-2-methylbenzoic acid

HRID 1416080Notes

Reaction equation

HRID 1416080 reaction equation
[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[OH-].[Na+].[C:14](OC(=O)C)(=[O:16])[CH3:15].Cl>>[C:14]([O:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])(=[O:16])[CH3:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 2520233-Hydroxy-2-methylbenzoic Acid

Product 1

HCID 37985573-Acetoxy-2-methylbenzoic acidYield 90%

Conditions

Temperature
5 °C

Procedure

60.9 g (0.40 mol) of 3-hydroxy-2-methylbenzoic acid are introduced into 500 ml of 2N sodium hydroxide solution (1.00 mol) with stirring and the solution formed in the course of this is cooled to 5° C. 61.3 g (0.60 mol) of acetic anhydride are added to the cooled solution. The reaction mixture is cooled here such that the temperature does not exceed 8° C. The reaction mixture is then acidified with 88 ml of 37% hydrochloric acid. The precipitated product is filtered off, washed three times with 50 ml of water and dried in vacuo. 69.9 g of 3-acetoxy-2-methylbenzoic acid are obtained. This corresponds to a yield of 90.0% of theory.

Workup

  1. customthe solution formed in the course of
  2. temperatureThe reaction mixture is cooled here such that the temperature
  3. customdoes not exceed 8° C
  4. filtrationThe precipitated product is filtered off
  5. washwashed three times with 50 ml of water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-943bed0e65b44d3fa0ce8925c869d307
Source dataset
uspto-grants-1999_06
Patent number
US05910605

Reaction notes

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