Potassium Hydroxide → HCID 15462302, compound

HRID 376517Notes

Reaction equation

HRID 376517 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]([C:17]([O:19]CC)=[O:18])[C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]([C:17]([OH:19])=[O:18])[C:10]=2[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15462300HCID 15462300, compound

Product 1

HCID 15462302HCID 15462302, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(3-chloro-phenyl)-3-phenyl-cycloprop-2-ene-1-carboxylate (0.55 g, 1.84 mmol) and potassium hydroxide (0.5 g, 9.25 mmol) were dissolved in methanol (20 cm3) and heated to reflux for 2 hours. The mixture was cooled to room temperature and the solvent evaporated. The residue was partitioned between water (30 cm3) and ethyl acetate (30 cm3). The aqueous layer was separated and washed with ethyl acetate (2×30 cm3) before being acidified to pH=1 with dilute hydrochloric acid and extracted with dichloromethane (3×40 cm3). The combined dichloromethane extracts were dried (MgSO4), evaporated, and washed with heptane to give the cyclopropene acid 0.21 g, 42%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customthe solvent evaporated
  4. customThe residue was partitioned between water (30 cm3) and ethyl acetate (30 cm3)
  5. customThe aqueous layer was separated
  6. washwashed with ethyl acetate (2×30 cm3)
  7. extractionextracted with dichloromethane (3×40 cm3)
  8. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  9. customevaporated
  10. washwashed with heptane

Sources & evidence

ORD record
ord-6f30e05e6ccb4059a46eb9fb87cda453
Source dataset
uspto-grants-2000_02
Patent number
US06020519

Reaction notes

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