Sodium Hydroxide → 7-Chloro-1-benzothiophene-2-carboxylic acid

HRID 2267471Notes

Reaction equation

HRID 2267471 reaction equation
[Cl:1][C:2]1[C:7]2[S:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[C:7]2[S:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22474203Methyl 7-chlorobenzo[b]thiophene-2-carboxylate

Product 1

HCID 101982427-Chloro-1-benzothiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 7-chlorobenzo[b]thiophene-2-carboxylate (3 g, 13 mmol) was dissolved is ethanol (15 mL) and treated 5 N sodium hydroxide (5 mL). The reaction was heated at reflux overnight. The volatiles were removed in vacuo and the aqueous residue was acidified to pH 2 using 5 N HCl. The resulting white solid was filtered off, washed well with water and dried in a vacuum oven at 60° C. Yield=2.6 g. MS (M−H)-210.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. customThe volatiles were removed in vacuo
  4. filtrationThe resulting white solid was filtered off
  5. washwashed well with water
  6. customdried in a vacuum oven at 60° C

Sources & evidence

ORD record
ord-313ebc139e5d47089c3e41446d6df94d
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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