p-Toluenesulfonic acid monohydrate → Benzo[b]thiophene-5-acetic acid

HRID 2390962Notes

Reaction equation

HRID 2390962 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10](C(O)=O)[C:11]([OH:13])=[O:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([OH:13])=[O:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 576150412-(1-Benzothiophen-5-yl)malonic acid

Product 1

HCID 11469582Benzo[b]thiophene-5-acetic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To xylene (2 mL) suspension of 0.10 g of 2-(1-benzothiophen-5-yl)malonic acid was added 4 mg of p-toluenesulfonic acid monohydrate, which was then refluxed for 1 hour. The solvent was distilled off under reduced pressure, and to the resultant residue was added cyclohexane. The precipitate was collected by filtration to provide 0.08 g of 2-(1-benzothiophen-5-yl)acetic acid as white solid form.

Workup

  1. temperaturewas then refluxed for 1 hour
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionto the resultant residue was added cyclohexane
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-d153fde41fd2405e971d797d8234b1e8
Source dataset
uspto-grants-2012_09
Patent number
US08273902B2

Reaction notes

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