Water → 4-[4-Sulfonylpyranoyloxy]-2-methoxybenzoic acid

HRID 1698

Reaction equation

HRID 1698 reaction equation
[S:1](=[C:4]1[CH:9]=[CH:8][O:7][C:6]([C:10]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[C:15]([O:23][CH3:24])[CH:14]=2)=[O:11])=[CH:5]1)(=[O:3])=[O:2].O.O[Li].O>C1COCC1>[S:1](=[C:4]1[CH:9]=[CH:8][O:7][C:6]([C:10]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:23][CH3:24])[CH:14]=2)=[O:11])=[CH:5]1)(=[O:2])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86752226Methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate

Product 1

HCID 867522274-[4-Sulfonylpyranoyloxy]-2-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred solution of methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate (470 mg, 1.5 mmol)in THF:H2O (18 mL: 2 mL) was added LiOH.H2O (128 mg, 3 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid passed through a plug of silca gel packed in 80:20 hexanes:EtOAc and eluted with same. The solvent was removed under reduced pressure to afford 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoic acid as a white solid.

Workup

  1. temperaturecooled to ambient temperature
  2. customThe solvent was removed under reduced pressure
  3. washEtOAc and eluted with same
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-633f98fd12d84e92930ec5dccc1d3957
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Linked notes

Loading…