Chloroacetic Acid → Benzo(b)thiophene-2-carboxylic acid

HRID 488058Notes

Reaction equation

HRID 488058 reaction equation
CC1C=CC=CC=1C=[S:5].Cl[CH2:11][C:12]([OH:14])=[O:13].[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[S:5]1[C:11]([C:12]([OH:14])=[O:13])=[CH:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=2

Participants

4

Reactant 3

HCID 300Chloroacetic AcidHCID 1140TolueneHCID 21897297HCID 21897297, compound

Product 1

HCID 95864Benzo(b)thiophene-2-carboxylic acidYield 80%

Conditions

Temperature
110 °C

Procedure

A four-necked flask (300 ml capacity) equipped with a stirrer, thermometer and condenser was charged with 30.4 g (0.20 mol) of 2-methylthiobenzaldehyde and 28.4 g (0.30 mol) of monochloroacetic acid and the reaction was conducted with stirring at 110° C. for about 10 hours. After completion of the reaction, 150 g of toluene was added to dissolve the reaction mixture and the solution was cooled for precipitation. The precipitate was collected by filtration and dried to give 28.5 g (yield 80%) of 2-benzo[b]thiophenecarboxylic acid as light yellow crystals.

Workup

  1. customA four-necked flask (300 ml capacity) equipped with a stirrer
  2. additionwas added
  3. dissolutionto dissolve the reaction mixture
  4. temperaturethe solution was cooled for precipitation
  5. filtrationThe precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-9f8acc067e4047e3b36f1c491229794c
Source dataset
uspto-grants-1994_03
Patent number
US05298630

Reaction notes

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