Sodium Hydroxide → 5-Methanesulfonylfuran-2-carboxylic acid

HRID 1698165Notes

Reaction equation

HRID 1698165 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:8][CH:9]=1)=[O:4].[OH-].[Na+]>CCO>[CH3:13][S:10]([C:7]1[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53485860Methyl 5-(methylsulfonyl)furan-2-carboxylate

Product 1

HCID 545928165-Methanesulfonylfuran-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-methanesulfonyl-furan-2-carboxylic acid methyl ester (2.94 g, 14.4 mmol) in EtOH (100 mL) was added a 2 N aqueous solution of sodium hydroxide (40 mL, 80 mmol). The mixture was warmed at 80° C. for 4 hours and then concentrated in vacuo to remove ethanol. The mixture was then acidified with 1 N aqueous HCl and extracted with ethyl acetate (4×30 mL). The combined organic layers were washed with brine (2×100 mL), dried over sodium sulfate, filtered and concentrated to afford 5-methanesulfonyl-furan-2-carboxylic acid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove ethanol
  3. extractionextracted with ethyl acetate (4×30 mL)
  4. washThe combined organic layers were washed with brine (2×100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c2357ad426a8431d97e39d8c9e1b7700
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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