Sodium Hydroxide → HCID 86624342, compound

HRID 2243805Notes

Reaction equation

HRID 2243805 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[C:8]([C:16]([O:18][CH3:19])=[O:17])[CH:9]=[C:10]([CH:15]=1)[C:11]([O:13]C)=[O:12])(=[O:4])=[O:3].[OH-].[Na+]>C1COCC1>[CH3:19][O:18][C:16]([C:8]1[CH:9]=[C:10]([CH:15]=[C:6]([O:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:7]=1)[C:11]([OH:13])=[O:12])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59569687HCID 59569687, compound

Product 1

HCID 86624342HCID 86624342, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of dimethyl 5-[(methylsulfonyl)oxy]isophthalate (1.37 g, 4.75 mmol) in THF (150 mL) was added 0.1 N NaOH solution (46.6 mL, 4.66 mmol) dropwise in an addition funnel. Reaction stirred at 0° C. for 2 hours and then warmed to room temperature. Reaction was concentrated in vacuo. Crude material was acidified with 1N HCl and extracted with EtOAc (3×). The combined organics were dried with MgSO4, filtered, concentrated and purified by flash chromatography (40 g silica, 0-5% MeOH/DCM/1% acetic acid) to give 0.74 g (57%) of 3-(methoxycarbonyl)-5-[(methylsulfonyl)oxy]benzoic acid. 1H NMR (400 MHz, CDCl3) δ 8.72 (m, 1H), 8.18 (m, 2H), 3.98 (s, 3H), 3.25 (s, 3H).

Workup

  1. customReaction
  2. temperaturewarmed to room temperature
  3. customReaction
  4. concentrationwas concentrated in vacuo
  5. extractionextracted with EtOAc (3×)
  6. dry with materialThe combined organics were dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography (40 g silica, 0-5% MeOH/DCM/1% acetic acid)

Sources & evidence

ORD record
ord-d1c949803b9c455f9f6b372c044a34d0
Source dataset
uspto-grants-2010_03
Patent number
US07678783B2

Reaction notes

Loading…