Methanol → Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

HRID 1375185Notes

Reaction equation

HRID 1375185 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].O=S(Cl)Cl.[CH3:16]O>>[CH3:16][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=1[OH:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 57882-Hydroxy-p-toluic acidHCID 24386Thionyl Chloride

Product 1

HCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl esterYield 72%

Conditions

Temperature
0 °C

Procedure

A 50 ml round-bottom flask equipped with a stir bar under a dry nitrogen atmosphere was charged with 4-methylsalicylic acid (1.5 g, 10.0 mmoles, 1.0 eq) followed by dry MeOH (15 ml). The reaction mixture was cooled to 0° C. on an ice bath and neat SOCl2 (1.1 ml, 15.0 mmoles, 1.5 eq) was added dropwise. The reaction was allowed to warm to room temperature and then stirred at reflux for 5 hrs. After that time, excess MeOH was removed in vacuo, the residue dissolved in EtOAc and extracted with saturated NaHCO3, the organic layer was dried with MgSO4 and filtered. Removal of excess solvent from the filtrate in vacuo provided 1.20 g (72%) of the title compound as a clear oil. (1H CDCl3, 400 MHz): δ 10.71 (s, 1H), 7.70 (d, J=8.1 Hz, 1H), 6.75 (s, 1H), 6.69 (d, J=8.1 Hz, 1H), 3.93 (s, 3H), 2.34 (s, 3H).

Workup

  1. customA 50 ml round-bottom flask equipped with a stir bar under a dry nitrogen atmosphere
  2. temperatureto warm to room temperature
  3. temperatureat reflux for 5 hrs
  4. customAfter that time, excess MeOH was removed in vacuo
  5. dissolutionthe residue dissolved in EtOAc
  6. extractionextracted with saturated NaHCO3
  7. dry with materialthe organic layer was dried with MgSO4
  8. filtrationfiltered
  9. customRemoval of excess solvent from the filtrate in vacuo

Sources & evidence

ORD record
ord-a968516bb6d046e490ad79c439652d2f
Source dataset
uspto-grants-2007_01
Patent number
US07166725B2

Reaction notes

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