Citric Acid → 6-(Methoxycarbonyl)benzo[b]thiophene-2-carboxylic acid

HRID 1172845Notes

Reaction equation

HRID 1172845 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.C(Cl)Cl>[CH3:17][O:16][C:14]([C:11]1[CH:12]=[CH:13][C:7]2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[S:9][C:8]=2[CH:10]=1)=[O:15]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 59556411Dimethyl benzo[b]thiophene-2,6-dicarboxylate

Product 1

HCID 595564196-(Methoxycarbonyl)benzo[b]thiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of benzo[b]thiophene-2,6-dicarboxylic acid dimethyl ester (139 mg, 0.56 mmol) in THF/MeOH (2/2 mL) was added 1 N NaOH (555 μL). After 5 h, the solution was diluted with CH2Cl2 and acidified with 5% citric acid. The combined organic fractions were dried, filtered, and concentrated to yield the desired acid, which was used without further purification. MS (EI): cal'd (MH+) 237.01, exp (MH+) 237.13.

Workup

  1. customThe combined organic fractions were dried
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-49a1533bf5f04cdcba4c4de59ad8e697
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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