Sodium Hydroxide → 5-(4-methoxyphenyl)thiophene-2-carboxylic Acid

HRID 1853934Notes

Reaction equation

HRID 1853934 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C:14]([O:16]C)=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 5150032Methyl 5-(4-methoxyphenyl)thiophene-2-carboxylate

Product 1

HCID 27641305-(4-methoxyphenyl)thiophene-2-carboxylic AcidYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 5-(4-methoxyphenyl)thiophene-2-carboxylate (1.4 g, 5.6 mmol), and 1 M sodium hydroxide (55 mL) in methanol (55 mL) was heated at 80° C. for 18 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid and aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the desired product (1.2 g, 93%) as an off-white solid: ESI MS m/z 325 [C12H10O3S+H]+.

Workup

  1. washThe organic layer was washed with 1 N hydrochloric acid and aqueous sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3a335dc183404774a7013bf78d99cbfe
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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