Sodium Hydroxide → 3-(benzyloxy)-2-thiophenecarboxylic acid

HRID 2115655Notes

Reaction equation

HRID 2115655 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14]([O:16]C)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 2764114methyl 3-(benzyloxy)-2-thiophenecarboxylate

Product 1

HCID 27667333-(benzyloxy)-2-thiophenecarboxylic acidYield 91.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(benzyloxy)-2-thiophenecarboxylate (7.85 g, 31.61 mmol) in MeOH (32 mL) and THF (16 mL) was added 2 N NaOH (21 mL), and the mixture was stirred at reflux for 10 hrs, and then concentrated under reduced pressure. The residue was diluted with water, washed with ether. The separated aqueous phase was acidified with 5N HCl. The precipitated solid was collected by filtration, washed with hexane, and dried under reduced pressure at 60° C. to give 3-(benzyloxy)-2-thiophenecarboxylic acid as a yellow solid (6.76 g, yield; 91%).

Workup

  1. temperatureat reflux for 10 hrs
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. washwashed with ether
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with hexane
  7. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-deab883940ce49a0bd6c946e4e540d37
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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