Hydrochloric Acid → 4-Benzo[b]thien-2-ylbenzoic acid

HRID 1096945Notes

Reaction equation

HRID 1096945 reaction equation
[OH-].[Na+].[S:3]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=2)=[CH:6][C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]1=2.Cl>CO>[S:3]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[CH:6][C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4137384Methyl 4-benzo[b]thien-2-ylbenzoate

Product 1

HCID 41373834-Benzo[b]thien-2-ylbenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous 5 N sodium hydroxide solution (0.28 mL, 1.40 mmol) was added to a methanol (2.3 mL) solution of methyl 4-(benzo[b]thiophen-2-yl)benzoate (124 mg, 0.462 mmol), and refluxed for 3 hours. After left cooled, 5 N hydrochloric acid (0.28 mL, 1.40 mmol) was added to the reaction mixture, and concentrated under reduced pressure. 20% methanol/THF was added to the residue, the mixture was filtered, and the filtrate was concentrated under reduced pressure. Diethyl ether was added to the residue, the insoluble matter was taken out through filtration, and dried to obtain the title compound as a pale yellow solid.

Workup

  1. temperaturerefluxed for 3 hours
  2. waitAfter left
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. addition20% methanol/THF was added to the residue
  6. filtrationthe mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionDiethyl ether was added to the residue
  9. filtrationthe insoluble matter was taken out through filtration
  10. customdried

Sources & evidence

ORD record
ord-aceecb72c08044efa61324c70ee2de39
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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