Potassium Hydroxide → 113589-47-2

HRID 621794Notes

Reaction equation

HRID 621794 reaction equation
[CH2:1]([O:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:6][C:5]=1[C:15]([O:17]C)=[O:16])[CH3:2].[OH-].[K+]>O1CCCC1.O>[CH2:1]([O:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:6][C:5]=1[C:15]([OH:17])=[O:16])[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 14154187HCID 14154187, compound

Product 1

HCID 14154196113589-47-2Yield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-ethoxy-5-phenyl-2-thiophenecarboxylate (12.0 g, 46 mmoles) in tetrahydrofuran (150 mL) is added to a solution of potassium hydroxide (14.6 g, 229 mmoles) in water (150 mL). The mixture is stirred and heated under reflux for 24 hours, then the tetrahydrofuran is removed using a rotary evaporator. The aqueous suspension is cooled in an ice bath and acidified with concentrated HCl. The precipitate is collected by filtration, rinsed well with water and dried to afford the pure product (10.6 g); mp 174°-175° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. customthe tetrahydrofuran is removed
  4. customa rotary evaporator
  5. temperatureThe aqueous suspension is cooled in an ice bath
  6. filtrationThe precipitate is collected by filtration
  7. washrinsed well with water
  8. customdried

Sources & evidence

ORD record
ord-92f96a21e97c471db183d0e02d89d7c9
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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