Potassium Hydroxide → 9-Chlorodibenzothiophene-3-acetic acid

HRID 1856524Notes

Reaction equation

HRID 1856524 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:22])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]3[C:16]([Cl:20])=[CH:17][CH:18]=[CH:19][C:14]=3[S:13][C:12]=2[CH:21]=1)C>C(O)C>[Cl:20][C:16]1[C:15]2[C:11]3[CH:10]=[CH:9][C:8]([CH2:7][C:6]([OH:22])=[O:5])=[CH:21][C:12]=3[S:13][C:14]=2[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 130651209-Chlorodibenzothiophene-3-acetic acid ethyl ester

Product 1

HCID 130651199-Chlorodibenzothiophene-3-acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 100 ml. flask, fitted with a condenser and containing a solution of 0.28 g. of potassium hydroxide in 50 ml. of ethanol was added 1.1 g. of 9-chlorodibenzothiophene-3-acetic acid ethyl ester. After the solution was refluxed for four hours, the solvent was removed in vacuo on the steam bath, the residue was dissolved in 50 ml. of water, and the aqueous solution was acidified with dilute hydrochloric acid. The product was filtered, washed with 20 ml. of water, and dried at 60° in a vacuum oven for 12 hours. The yield of 9-chlorodibenzothiophene-3-acetic acid, after crystallization from methanol, was 0.8 g. (m.p. 203°-206°).

Workup

  1. customflask, fitted with a condenser
  2. additioncontaining a solution of 0.28 g
  3. temperatureAfter the solution was refluxed for four hours
  4. customthe solvent was removed in vacuo on the steam bath
  5. dissolutionthe residue was dissolved in 50 ml
  6. filtrationThe product was filtered
  7. washwashed with 20 ml
  8. dry with materialof water, and dried at 60° in a vacuum oven for 12 hours
  9. customThe yield of 9-chlorodibenzothiophene-3-acetic acid, after crystallization from methanol

Sources & evidence

ORD record
ord-669e3e2bdfcc463689a09cb02a307163
Source dataset
uspto-grants-1980_08
Patent number
US04219657

Reaction notes

Loading…