Methanol → Methyl 4-chloro-2-hydroxybenzoate

HRID 893714Notes

Reaction equation

HRID 893714 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.S(=O)(=O)(O)O.[CH3:17]O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([OH:11])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 787824-Chlorosalicylic acid

Product 1

HCID 327085Methyl 4-chloro-2-hydroxybenzoateYield 88.6%

Procedure

A mixture of 4-chloro-2-hydroxybenzoic acid (200 g, 1.16 mol) and 40 ml conc. sulfuric acid in 400 ml of methanol was heated under reflux for 201/2 hours. The solvent was evaporated under reduced pressure, the residue poured into aqueous saturated Na2CO3, and then extracted with ethyl ether (3×500 ml). The combined organic layers were dried over anhydrous Na2SO4, and evaporated to give 2f (191.6 g, 88.6% yield) as an oil. This was used for the next reaction without purification. IR (neat) 3150 (OH), 1728 (C=0), and 1678 (C=0) cm-1. NMR (CDCl3) δ 10.27 (br s, 1H, OH), 7.47 (d, 1H, JBC =8 Hz, HC), 6.80 (d, 1H, JAB =2 Hz, HA), 6.63 (d of d, 1H, HB), and 3.85 (s, 3H, CH3).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 201/2 hours
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe residue poured into aqueous saturated Na2CO3
  5. extractionextracted with ethyl ether (3×500 ml)
  6. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-5dba1d8190e14b1fa5511170fc682062
Source dataset
uspto-grants-1992_06
Patent number
US05126364

Reaction notes

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