p-Toluenesulfonic acid monohydrate → 2-(1-Benzothiophen-5-yl)malonic acid

HRID 2390961Notes

Reaction equation

HRID 2390961 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:18]([O:20]C(C)(C)C)=[O:19])[C:11]([O:13]C(C)(C)C)=[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=CC=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:11]([OH:13])=[O:12])[C:18]([OH:20])=[O:19])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58239411Di(tert-butyl)2-(1-benzothiophen-5-yl)malonate

Product 1

HCID 576150412-(1-Benzothiophen-5-yl)malonic acidYield 82.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To toluene (2.5 mL) solution of 0.25 g of di(tert-butyl) 2-(1-benzothiophen-5-yl)malonate was added 0.01 g of p-toluenesulfonic acid monohydrate, which was then refluxed for 1 hour. After cooling the reaction mixture, the precipitate was collected by filtration to provide 0.14 g of 2-(1-benzothiophen-5-yl)malonic acid as white solid form.

Workup

  1. temperaturewas then refluxed for 1 hour
  2. temperatureAfter cooling the reaction mixture
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-054bd898c26843d5af008bce44cc61f2
Source dataset
uspto-grants-2012_09
Patent number
US08273902B2

Reaction notes

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