Potassium Hydroxide → 2,3-diphenylcycloprop-2-ene-1-carboxylic acid

HRID 1740064Notes

Reaction equation

HRID 1740064 reaction equation
[C:1]1([C:7]2[CH:8]([C:16]([O:18]CC)=[O:17])[C:9]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>CO>[C:10]1([C:9]2[CH:8]([C:16]([OH:18])=[O:17])[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 281943ethyl 2,3-diphenylcycloprop-2-ene-1-carboxylate

Product 1

HCID 3473832,3-diphenylcycloprop-2-ene-1-carboxylic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2,3-diphenyl-cycloprop-2-ene-1-carboxylate (1.75 g, 6.6 mol) and potassium hydroxide (1.79 g, 31.9 mmol) were dissolved in methanol (60 cm3) and heated to reflux for 5 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) and evaporated to give the cyclopropene acid 1.22 g, 78%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. customthe solvent evaporated
  4. customThe residue was partitioned between water (30 cm3) and ethyl acetate (30 cm3) The aqueous layer
  5. customwas 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

Sources & evidence

ORD record
ord-b717bd3b0e1c41278b5b4c639d257024
Source dataset
uspto-grants-1999_10
Patent number
US05968968

Reaction notes

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