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

HRID 376516Notes

Reaction equation

HRID 376516 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)
  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

Sources & evidence

ORD record
ord-a83301eba8374a419b6e6539399da309
Source dataset
uspto-grants-2000_02
Patent number
US06020519

Reaction notes

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