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

HRID 2426128Notes

Reaction equation

HRID 2426128 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 (25.42 g, 167 mmol, TCl US) and concentrated sulfuric acid (3 mL) in absolute ethanol (180 mL) was heated at reflux for 20 hours. After cooling, solid sodium bicarbonate (10 g) was added to neutralize the acid. The mixture was partitioned between diethyl ether (2×400 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 as white crystals in two crops. (Yield 29.14 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. temperatureAfter cooling
  4. customThe mixture was partitioned between diethyl ether (2×400 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-76bf4acf329e4fe0abb25cef0323bd0e
Source dataset
uspto-grants-2011_06
Patent number
US07968554B2

Reaction notes

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