Sodium Hydroxide → 8-Chlorodibenzothiophene-3-acetic acid

HRID 1856516Notes

Reaction equation

HRID 1856516 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:22])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]3[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=3[S:13][C:12]=2[CH:21]=1)C>C(O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]2[S:13][C:12]3[CH:21]=[C:8]([CH2:7][C:6]([OH:22])=[O:5])[CH:9]=[CH:10][C:11]=3[C:15]=2[CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 130650978-Chloro-dibenzothiophene-3-acetic acid ethyl ester

Product 1

HCID 130651048-Chlorodibenzothiophene-3-acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 500 ml. flask, fitted with a condenser and containing a solution of 1.84 g. of sodium hydroxide in 150 ml. of ethanol was added 14 g. of 8-chloro-dibenzothiophene-3-acetic acid ethyl ester. After the solution was refluxed for 1 hour, the solvent was removed in vacuo (steam bath, rotary evaporator), the residue dissolved in 100 ml. of water, and the aqueous solution acidified with dilute hydrochloric acid. The 8-chloro-dibenzothiophene-3-acetic acid was removed by filtration, washed with water and dried at 60° in a vacuum oven overnight. The yield of 8-chloro-dibenzothiophene-3-acetic acid, after crystallization from i-propanol, was 8 g., mp 220°-221°.

Workup

  1. customflask, fitted with a condenser
  2. additioncontaining a solution of 1.84 g
  3. temperatureAfter the solution was refluxed for 1 hour
  4. customthe solvent was removed in vacuo (steam bath, rotary evaporator)
  5. dissolutionthe residue dissolved in 100 ml
  6. customThe 8-chloro-dibenzothiophene-3-acetic acid was removed by filtration
  7. washwashed with water
  8. customdried at 60° in a vacuum oven overnight
  9. customThe yield of 8-chloro-dibenzothiophene-3-acetic acid, after crystallization from i-propanol

Sources & evidence

ORD record
ord-5ccebfc77e6641aea9ff11c8b30c9550
Source dataset
uspto-grants-1980_08
Patent number
US04219657

Reaction notes

Loading…