Hydrochloric Acid → HCID 19851617, compound

HRID 1583580Notes

Reaction equation

HRID 1583580 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([O:17][CH2:18][CH2:19][CH3:20])=[CH:6][C:7]2[S:11][C:10]([C:12]([O:14]C)=[O:13])=[CH:9][C:8]=2[CH:16]=1)[CH3:2].[OH-].[K+].O.Cl>C(O)C>[CH2:1]([O:3][C:4]1[C:5]([O:17][CH2:18][CH2:19][CH3:20])=[CH:6][C:7]2[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][C:8]=2[CH:16]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 20259226HCID 20259226, compound

Product 1

HCID 19851617HCID 19851617, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.45 g. of methyl 5-ethoxy-6-propyloxybenzothiophene-2-carboxylate and 0.34 g. of potassium hydroxide in ethanol was heated to reflux for two hours. The solution was poured into water, acidified with hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was extracted with 1N sodium hydroxide. The alkaline solution was acidified with hydrochloric acid and was then extracted with ethyl acetate. The organic extract was dried over sodium sulfate and evaporated in vacuo to provide the desired title product, m.p. 192°-194° C., in an overall molar yield of 36% from 5-ethoxy-6-hydroxybenzothiophene-2-carboxylic acid.

Workup

  1. temperatureto reflux for two hours
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate layer was extracted with 1N sodium hydroxide
  4. extractionwas then extracted with ethyl acetate
  5. extractionThe organic extract
  6. dry with materialwas dried over sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-0873bdd03a42414a819ec017e436b3c1
Source dataset
uspto-grants-1985_11
Patent number
US04552891

Reaction notes

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