Potassium Hydroxide → HCID 22272245, compound

HRID 1064219Notes

Reaction equation

HRID 1064219 reaction equation
[C:1]1([C:7]2[C:8]3([C:14]([O:16]CC)=[O:15])[CH2:13][C:11]([CH:12]=2)=[CH:10][CH2:9]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>CO>[C:1]1([C:7]2[C:8]3([C:14]([OH:16])=[O:15])[CH2:13][C:11]([CH:12]=2)=[CH:10][CH2:9]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22272243HCID 22272243, compound

Product 1

HCID 22272245HCID 22272245, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Next, 2-phenyl-norbornadiene-1-carboxylic acid was synthesized. Ethyl 2-phenyl-norbornadiene-1-carboxylate (5.0 g) was combined with 3.8 g of potassium hydroxide in 50 mL of methanol. This solution was stirred at gentle reflux for 16 hours. All methanol was then removed by rotary evaporation, and the resulting residue was dissolved in 75 mL water. To this solution was added 10% HCl (aq) dropwise until the pH of the solution was acidic. The resulting yellow solid was collected by filtration. Recrystallization of this residue from isopropyl alcohol/water (40/60) gave 2.6 g of colorless needles in two crops (60% of theoretical). This intermediate product was characterized by NMR and by mass spectroscopy. 1H NMR (CDCl3) δ 7.54-7.50 (m, 2H); 7.39-7.32 (m, 3H); 7.02-6.99 (m, 1H); 6.93-6.90 (m, 1H); 4.08 (s, 1H); 3.87 (s, 1H); 2.27 (d, 1H); 2.08 (d, 1H).

Workup

  1. temperatureat gentle reflux for 16 hours
  2. customAll methanol was then removed by rotary evaporation
  3. dissolutionthe resulting residue was dissolved in 75 mL water
  4. additionTo this solution was added 10% HCl (aq) dropwise until the pH of the solution
  5. filtrationThe resulting yellow solid was collected by filtration
  6. customRecrystallization of this residue from isopropyl alcohol/water (40/60)

Sources & evidence

ORD record
ord-809be3d0846f48229a6f22b207609643
Source dataset
uspto-grants-2005_11
Patent number
US06969578B2

Reaction notes

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