Water → HCID 18989204, compound

HRID 2395562Notes

Reaction equation

HRID 2395562 reaction equation
[Cl:1][C:2]1[C:10]2[C:9]([O:11][CH3:12])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:13]([O:15]C)=[O:14].O.[OH-].[Li+].O>CO>[Cl:1][C:2]1[C:10]2[C:9]([O:11][CH3:12])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 18989147HCID 18989147, compound

Product 1

HCID 18989204HCID 18989204, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-chloro-3-methoxybenzo[b]thiophene-5-carboxylate (8.35 g) and lithium hydroxide hydrate (1.37 g) was stirred in methanol (75 ml) and water (25 ml) at room temperature for 4 days. The methanol was evaporated in vacuo and the mixture poured onto excess cold dilute hydrochloric acid. The solid was filtered, washed with cold cyclohexane and dried to give 4-chloro-3-methoxybenzo[b]thiophene-5-carboxylic acid (7.28 g) as a white solid, NMR (d6DMSO) δ3.9(3H,s), 7.0(1H,s), 7.6(1H,d), 7.95(1H,d), 13.3(1H,brs).

Workup

  1. customThe methanol was evaporated in vacuo
  2. additionthe mixture poured onto excess cold dilute hydrochloric acid
  3. filtrationThe solid was filtered
  4. washwashed with cold cyclohexane
  5. customdried

Sources & evidence

ORD record
ord-b7345dc6bbd444a8b1ac9d1b9ace6e52
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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