HCID 14919052, compound → Ethyl 2-hydroxy-4-(methylsulfonyl)benzoate

HRID 2303468Notes

Reaction equation

HRID 2303468 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][C:5]=1[O:14]C.Cl.[NH+]1C=CC=C[CH:19]=1>>[CH2:1]([O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][C:5]=1[OH:14])[CH3:19]

Participants

3

Reactant 2

HCID 14919052HCID 14919052, compoundHCID 21584435Pyridinium hydrochloride

Product 1

HCID 69908919Ethyl 2-hydroxy-4-(methylsulfonyl)benzoateYield 56.7%

Conditions

Temperature
180 °C

Procedure

A mixture of 10 (15 g) and pyridinium hydrochloride (45 g) was heated under an inert atmosphere at 180° C. for 1.5 h and cooled. The mixture was partitioned between EtOAc and aqueous HCl (5%). The organic layer was washed with aqueous HCl (5%), dried, filtered, and concentrated. A solution of the resulting residue in EtOH (400 mL) was treated with concentrated H2SO4 (10 mL) and heated overnight at 75° C. After cooling, the mixture was concentrated and partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was extracted with 1 M NaOH (4 times). This combined aqueous layer was brought to acidic pH by addition of aqueous HCl (5%) and was extracted with EtOAc. This organic layer was dried (MgSO4), filtered, and evaporated giving 8.5 g of 2-hydroxy-4-methanesulfonyl-benzoic acid ethyl ester 11 as a solid.

Workup

  1. temperaturecooled
  2. customThe mixture was partitioned between EtOAc and aqueous HCl (5%)
  3. washThe organic layer was washed with aqueous HCl (5%)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionA solution of the resulting residue in EtOH (400 mL) was treated with concentrated H2SO4 (10 mL)
  8. temperatureheated overnight at 75° C
  9. temperatureAfter cooling
  10. concentrationthe mixture was concentrated
  11. custompartitioned between EtOAc and saturated aqueous NaHCO3
  12. extractionThe organic layer was extracted with 1 M NaOH (4 times)
  13. additionThis combined aqueous layer was brought to acidic pH by addition of aqueous HCl (5%)
  14. extractionwas extracted with EtOAc
  15. dry with materialThis organic layer was dried (MgSO4)
  16. filtrationfiltered
  17. customevaporated

Sources & evidence

ORD record
ord-047e8920a89c40209db31ab34862e15b
Source dataset
uspto-grants-2002_08
Patent number
US06433005B1

Reaction notes

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