Potassium Hydroxide → HCID 14330447, compound

HRID 2292158Notes

Reaction equation

HRID 2292158 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([CH2:10][C:11]([O:13]CC)=[O:12])=[C:8]([S:16][CH2:17][C:18]([O:20]CC)=[O:19])[CH:7]=[CH:6][CH:5]=1)[CH3:2].[OH-].[K+]>C(O)C.O>[CH2:1]([O:3][C:4]1[C:9]([CH2:10][C:11]([OH:13])=[O:12])=[C:8]([S:16][CH2:17][C:18]([OH:20])=[O:19])[CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 14330446HCID 14330446, compound

Product 1

HCID 14330447HCID 14330447, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 6-ethoxy-2-(ethoxycarbonylmethylthio)-phenylacetate (17.8 g) in ethanol (112 mL) is added a solution of potassium hydroxide (85%, 7.21 g) in water (28 mL). The solution is refluxed for 2 hours, is concentrated in vacuo to remove the ethanol, and is diluted with water (200 mL). Hydrochloric acid (12N, 10.0 mL) is added. The product which originally precipitates as an oil slowly crystallizes. After crystallization is complete the solid is filtered off, air-dried for 2 hours and then dried in vacuo at 50° to obtain 6-ethoxy-2-(carboxymethylthio)phenylacetic acid, m.p. 147°-150°.

Workup

  1. temperatureThe solution is refluxed for 2 hours
  2. concentrationis concentrated in vacuo
  3. customto remove the ethanol
  4. additionis diluted with water (200 mL)
  5. additionHydrochloric acid (12N, 10.0 mL) is added
  6. customThe product which originally precipitates as an oil
  7. customslowly crystallizes
  8. customAfter crystallization
  9. filtrationis filtered off
  10. customair-dried for 2 hours
  11. customdried in vacuo at 50°

Sources & evidence

ORD record
ord-379f27b8d8f6473ca108da2214a9c707
Source dataset
uspto-grants-1989_01
Patent number
US04801605

Reaction notes

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