Methanol → Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

HRID 477483Notes

Reaction equation

HRID 477483 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[CH3:17]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:17])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric Acid2×HCID 94475-Chlorosalicylic Acid

Product 1

HCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl esterYield 94.8%

Procedure

A mixture of 5-chloro-2-hydroxybenzoic acid (100 g, 0.57 mol), 20 ml of conc. H2SO4 and 200 ml of dry methanol was heated under reflux for 22 hours. An additional 5 ml of conc. H2SO4 was then added and the solution heated for an additional 24 hours. The solvent was evaporated under reduced pressure and the resulting residue poured into aqueous saturated Na2CO3 and then extracted with CH2Cl2 (2×400 ml). The organic layers were combined, dried over anhydrous Na2SO4, and evaporated to give the desired compound as a white solid (100.5 g, 94.8% yield), mp 44°-46° C. IR (nujol) 1680 (ester) cm-1. NMR (CDCl3) δ 10.60 (s, 1H, OH), 7.73 (d, 1H, JBC =3 Hz HC), 7.33 (d of d, 1H, JAB =9 Hz, HB), 6.87 (d, 1H, HA), and 3.92 (s, 3H, CH3).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 22 hours
  3. temperaturethe solution heated for an additional 24 hours
  4. customThe solvent was evaporated under reduced pressure
  5. additionthe resulting residue poured into aqueous saturated Na2CO3
  6. extractionextracted with CH2Cl2 (2×400 ml)
  7. dry with materialdried over anhydrous Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-780f84e57cef4018b604f2b2b3ff2e60
Source dataset
uspto-grants-1989_12
Patent number
US04888353

Reaction notes

Loading…