Ethanol → 3-HYDROXY-4-METHYLBENZOIC ACID ETHYL ESTER

HRID 2426115Notes

Reaction equation

HRID 2426115 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:22](O)[CH3:23]>>[CH2:22]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([OH:1])[CH:3]=1)[CH3:23]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 685123-Hydroxy-4-methylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 157454893-HYDROXY-4-METHYLBENZOIC ACID ETHYL ESTER

Procedure

A mixture of 3-hydroxy-4-methylbenzoic acid (25.0 g, 164 mmol, Aldrich) and concentrated sulfuric acid (3 mL) in absolute ethanol (165 mL) was heated at reflux for 20 hours. After cooling, solid sodium bicarbonate (7 g) was added to neutralize the acid. The mixture was then partitioned between diethyl ether (2×300 mL) and water (2×300 mL). The organic layers were washed with brine (300 mL), combined, dried (MgSO4), filtered, and concentrated. The residue was recrystallized from hexanes to give 3-hydroxy-4-methyl-benzoic acid ethyl ester in two crops as white crystals. (Yield 28.90 g, 97.8%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. temperatureAfter cooling
  4. customThe mixture was then partitioned between diethyl ether (2×300 mL) and water (2×300 mL)
  5. washThe organic layers were washed with brine (300 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was recrystallized from hexanes

Sources & evidence

ORD record
ord-f4f61067cdbf4a759937044ce852072d
Source dataset
uspto-grants-2011_06
Patent number
US07968554B2

Reaction notes

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