Sodium Hydroxide → 1-Benzothiophene-7-carboxylic acid

HRID 605953Notes

Reaction equation

HRID 605953 reaction equation
C([O:3][C:4]([C:6]1[C:11]2[S:12][CH:13]=[CH:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>CO.O>[S:12]1[CH:13]=[CH:14][C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:11]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 49758023Ethyl benzo[b]thiophene-7-carboxylate

Product 1

HCID 142350731-Benzothiophene-7-carboxylic acidYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of benzo[b]thiophene-7-carboxylic acid ethyl ester (1.0 g, 48 mmol) in methanol (10 mL) and water (10 mL) is added sodium hydroxide (5 g, excess). The solution is stirred at room temperature for 30 min; at which point all the ester has been consumed. The reaction mixture is adjusted to pH 1 by adding 6M HCl solution, and extracted with DCM. The combined organic layers are filtered through a silica plug to afford the title compound as a yellow solid (505.2 mg, 59%).

Workup

  1. customat which point all the ester has been consumed
  2. additionby adding 6M HCl solution
  3. extractionextracted with DCM
  4. filtrationThe combined organic layers are filtered through a silica plug

Sources & evidence

ORD record
ord-d91cd1895e324c6aaf09b9b5c1880d06
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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