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

HRID 2081065Notes

Reaction equation

HRID 2081065 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. Mixture was partitioned between diethyl ether (2×400 mL) and water (2×300 mL). Organic layers were washed with brine (300 mL), combined, dried (MgSO4), filtered, and concentrated. 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, 96.8%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. temperatureAfter cooling
  4. customMixture was partitioned between diethyl ether (2×400 mL) and water (2×300 mL)
  5. washOrganic layers were washed with brine (300 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customResidue was recrystallized from hexanes

Sources & evidence

ORD record
ord-241ad2865b934f63891cfdc56fcebda0
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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