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

HRID 1975669Notes

Reaction equation

HRID 1975669 reaction equation
S(Cl)(Cl)=O.[CH3:5]O.[Cl:7][C:8]1[CH:16]=[C:12]([C:13]([OH:15])=[O:14])[C:11]([OH:17])=[CH:10][CH:9]=1>>[Cl:7][C:8]1[CH:16]=[C:12]([C:13]([O:15][CH3:5])=[O:14])[C:11]([OH:17])=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 94475-Chlorosalicylic AcidHCID 24386Thionyl Chloride

Product 1

HCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Conditions

Temperature
-5 °C

Procedure

Thionyl chloride (900 g, 7.56 mol) is added dropwise to methanol (1977 g, 61.72 mol) at 20° C. over a period of 1.5 hours, maintaining the temperature between 15°-25° C. with an ice bath. The cooling bath is removed and 5-chlorosalicylic acid (1000 g, 5.8 mol) added in one portion, then slowly heated to reflux. On completion of the reaction the solution is cooled to -5° C. for 1 hour. The methyl 5-chlorosalicylate is filtered, washed with cold methanol (150 ml) and dionized water (2×1 L). The solid is dried under house vacuum at 30° C. for 24 hours to give methyl 5-chlorosalicylate; m.p. 44°-46° C.

Workup

  1. temperaturemaintaining the temperature between 15°-25° C. with an ice bath
  2. customThe cooling bath is removed
  3. temperatureslowly heated to reflux
  4. customOn completion of the reaction the solution
  5. filtrationThe methyl 5-chlorosalicylate is filtered
  6. washwashed with cold methanol (150 ml) and dionized water (2×1 L)
  7. customThe solid is dried under house vacuum at 30° C. for 24 hours

Sources & evidence

ORD record
ord-f91214f4a8944743b2c82e5440bc9072
Source dataset
uspto-grants-1994_02
Patent number
US05288731

Reaction notes

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