Potassium Hydroxide → HCID 19362297, compound

HRID 1740066Notes

Reaction equation

HRID 1740066 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([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:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15462304HCID 15462304, compound

Product 1

HCID 19362297HCID 19362297, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(4-chlorophenyl)-3-phenyl-cycloprop-2-ene-1-carboxylate (0.66 g, 2.20 mmol) and potassium hydroxide (0.7 g, 12.95 mmol) were dissolved in methanol (25 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 0.27 g, 45%.

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-123710dcd84c42b599236ab2a05f2c2e
Source dataset
uspto-grants-1999_10
Patent number
US05968968

Reaction notes

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