Hydrochloric Acid → 2-Hydroxy-5-methylsulfonylbenzoic acid methyl ester

HRID 1835123Notes

Reaction equation

HRID 1835123 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:16]O>>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 124227802-Hydroxy-5-(methylsulfonyl)benzoic acid

Product 1

HCID 235031632-Hydroxy-5-methylsulfonylbenzoic acid methyl esterYield 71%

Procedure

A solution of 2-hydroxy-5-(methylsulfonyl)benzoic acid (5.80 g, 26.8 mmol, prepared using procedure in J. Chem. Soc., Perkin Trans 1 1978, 6, 633-638) in MeOH (150 ml) at 0° C. was saturated with HCl (g). The solution was warmed to r.t. and heated to reflux for 3 h. The solid which formed upon cooling was filtered and dried to afford the title compound (4.40 g, 19.1 mmol, 71%).

Workup

  1. customat 0° C.
  2. temperatureheated
  3. temperatureto reflux for 3 h
  4. customThe solid which formed
  5. temperatureupon cooling
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-c6eefa93d61c4eb29f733d8ad553f043
Source dataset
uspto-grants-2004_08
Patent number
US06770645B2

Reaction notes

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