Acetyl chloride → Methyl 3-hydroxy-2-methylbenzoate

HRID 2188008Notes

Reaction equation

HRID 2188008 reaction equation
[C:1](Cl)(=O)C.[OH:5][C:6]1[C:7]([CH3:15])=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10]>CO>[CH3:1][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[C:6]([OH:5])[C:7]=1[CH3:15]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 2520233-Hydroxy-2-methylbenzoic Acid

Product 1

HCID 12488879Methyl 3-hydroxy-2-methylbenzoateYield 87.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (5.4 ml, 5.96 g, 76 mmol) was added dropwise to methanol (15 ml) at 0° C. in a sealed 50 ml round-bottom flask. This solution was allowed to warm to room temperature for 1 hour while stirring. To this solution 3-hydroxy-2-methyl-benzoic acid (519 mg, 3.4 mmol) was added and the solution was stirred at room temperature for 42 hours. The reaction was quenched with saturated aqueous sodium bicarbonate and solid sodium bicarbonate. The volatiles were removed in vacuo and the basic aqueous solution was then extracted with dichloromethane (4×40 ml). The combined organic extracts were dried (MgSO4), filtered, and the solvent evaporated in vacuo affording 493 mg (87%) of 3-hydroxy-2-methyl-benzoic acid methyl ester as a solid.

Workup

  1. stirringthe solution was stirred at room temperature for 42 hours
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate and solid sodium bicarbonate
  3. customThe volatiles were removed in vacuo
  4. extractionthe basic aqueous solution was then extracted with dichloromethane (4×40 ml)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-f5349e10e8de4f9182c8a77c634ae1c3
Source dataset
uspto-grants-2002_06
Patent number
US06410556B1

Reaction notes

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