Ethanol → Ethyl 3-hydroxy-2-methylbenzoate

HRID 1678597Notes

Reaction equation

HRID 1678597 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].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:17][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2520233-Hydroxy-2-methylbenzoic Acid

Product 1

HCID 15376194Ethyl 3-hydroxy-2-methylbenzoateYield 95%

Procedure

To a solution of 3-hydroxy-2-methylbenzoic acid (1.00 g, 6.57 mmol) in ethanol (10 mL) was added sulfuric acid (0.16 g, 1.64 mmol), and the mixture was heated under reflux for 12 hours. The reaction solution was cooled to room temperature, and one half of the solvent was concentrated under reduced pressure. Then, water (30 mL) was added thereto, and the mixture was neutralized with sodium carbonate. The mixture was extracted with diethyl ether, and the organic layer was washed with water, and then concentrated under reduced pressure. To the resulting residue was added hexane and crystallized to give the title compound (1.12 g, yield 95%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. concentrationone half of the solvent was concentrated under reduced pressure
  4. additionThen, water (30 mL) was added
  5. extractionThe mixture was extracted with diethyl ether
  6. washthe organic layer was washed with water
  7. concentrationconcentrated under reduced pressure
  8. additionTo the resulting residue was added hexane
  9. customcrystallized

Sources & evidence

ORD record
ord-6628b428d5b744c69d072a3be559b018
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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