Sodium Hydroxide → 3-Benzyloxy-5-(methylsulfonyl)-2-thiophenecarboxylic Acid

HRID 1953964Notes

Reaction equation

HRID 1953964 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[S:11][C:10]=1[C:18]([O:20]C)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[S:11][C:10]=1[C:18]([OH:20])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15477099Methyl 3-Benzyloxy-5-(methylsulfonyl)-2-thiophenecarboxylate

Product 1

HCID 154771003-Benzyloxy-5-(methylsulfonyl)-2-thiophenecarboxylic AcidYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-benzyloxy-5-(methylsulfonyl)-2-thiophenecarboxylate (16.7 g, 51.2 mmol), 50 ml 2N NaOH and 50 ml of tetrahydrofuran is heated at reflux temperatures for 1 hour, cooled to room temperature and concentrated in vacuo to an aqueous residue. The residue is diluted with water, acidified to pH 1-2 with 6N HCl and filtered. The filtercake is washed with water and dried to give the title product as a white solid, 14.55 g (91% yield). A small sample was recrystallized from aqueous ethanol to give white needles, mp 188-189° C., identified by 1HNMR, 13CNMR, IR and mass spectral analyses.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperatures for 1 hour
  3. concentrationconcentrated in vacuo to an aqueous residue
  4. additionThe residue is diluted with water
  5. filtrationfiltered
  6. washThe filtercake is washed with water
  7. customdried

Sources & evidence

ORD record
ord-0427b91fb64346f7a779dd283a6de8a2
Source dataset
uspto-grants-2000_09
Patent number
US06121202

Reaction notes

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