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

HRID 1699

Reaction equation

HRID 1699 reaction equation
[S:1](=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7][CH:6]([C:14]([O:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[C:19]([O:27][CH3:28])[CH:18]=2)=[O:15])[CH2:5]1)(=[O:3])=[O:2].O.O[Li].O>C1COCC1>[S:1](=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7][CH:6]([C:14]([O:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[C:19]([O:27][CH3:28])[CH:18]=2)=[O:15])[CH2:5]1)(=[O:2])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 19691028Methyl 4-[4-sulfonylchromanoyloxy]-2-methoxybenzoate

Product 1

HCID 196909464-[4-Sulfonylchromanoyloxy]-2-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred solution of methyl 4-[4-sulfonylchromanoyloxy]-2-methoxybenzoate (500 mg, 1.38 mmol) in THF:H2O (18 mL: 2 mL) was added LiOH.H2O (175 mg, 4.14 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 was passed through a plug of silca gel packed in 50:50 MeOH:CH2Cl2 and eluted with same. The solvent was removed under reduced pressure to afford 4-[4-sulfonylchromanoyloxy]-2-methoxybenzoic acid as a white solid.

Workup

  1. temperaturecooled to ambient temperature
  2. customThe solvent was removed under reduced pressure
  3. washCH2Cl2 and eluted with same
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-46bdac7b5dca4dd2b9ea60dfb2c0fdfb
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Linked notes

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