Potassium Hydroxide → 9-Chlorodibenzothiophene-3-acetic acid

HRID 1156169Notes

Reaction equation

HRID 1156169 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 over 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 over for 12 hours
  9. customThe yield of 9-chlorodibenzothiophene-3-acetic acid, after crystallization from methanol

Sources & evidence

ORD record
ord-0c815fd9e5be4a63b21f7d665182c4fe
Source dataset
uspto-grants-1982_06
Patent number
US04334078

Reaction notes

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