Sodium Hydroxide → 3-{[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]sulfonyl}benzoic acid

HRID 968766Notes

Reaction equation

HRID 968766 reaction equation
[S:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])([OH:3])=[O:2].[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:19][CH2:20][CH2:21]I.[OH-].[Na+]>O.C(O)C>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:19][CH2:20][CH2:21][S:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(=[O:3])=[O:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 111186622H-Pyran, tetrahydro-2-(2-iodoethoxy)-HCID 219411183-Sulfinobenzoic acid

Product 1

HCID 695224113-{[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]sulfonyl}benzoic acidYield 14.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 3-sulfino-benzoic acid (1 g) and 2-iodoethyl tetrahydro-2H-pyran-2-yl ether (1.4 g) in water (20 ml) and ethanol (20 ml) was added NaOH solution to give a pH of 9. The resulting mixture was refluxed for 3 hours before evaporation of the ethanol. The aqueous was acidified to pH3 and the product extracted with EtOAc. The organic layer was separated, dried with MgSO4 and solvent removed by evaporation to give the sub-title compound (0.25 g).

Workup

  1. customto give a pH of 9
  2. extractionthe product extracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried with MgSO4 and solvent
  5. customremoved by evaporation

Sources & evidence

ORD record
ord-3c23b48ddc334ca4b63f157b93c14c02
Source dataset
uspto-grants-2007_12
Patent number
US07304077B2

Reaction notes

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