Potassium Hydroxide → HCID 86733832, compound

HRID 1283494Notes

Reaction equation

HRID 1283494 reaction equation
[C:1]12[CH2:7][C:4]([CH2:5][CH2:6]1)=[CH:3][CH:2]=2.C([CH:12]=[C:13]([C:17]#[N:18])[C:14]([OH:16])=[O:15])C(C)C.[OH-].[K+]>O>[C:1]12[CH2:7][C:4]([CH2:5][CH2:6]1)=[CH:3][CH:2]=2.[C:17]([C:13](=[CH2:12])[C:14]([OH:16])=[O:15])#[N:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86733833HCID 86733833, compound

Product 1

HCID 86733832HCID 86733832, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a flask fitted with a condenser and magnetic stirring bar is charged 12.3 g (0.05 mole) norbornadiene/isobutyl 2-cyanoacrylic acid adduct and a solution of 4.9 g 86% potassium hydroxide (0.075 mole) in 75 ml. of water. After heating at reflux for 1.5 hours, the solution is cooled to room temperature and extracted with 2 × 25 ml. of hexane to remove any nonsaponified adduct. The aqueous phase is acidified to pH 2 with 6 N hydrochloric acid and the liberated oily product is taken up in 100 ml. ethyl acetate. The extract is filtered to remove some white insoluble solids (0. 9g., m.p. 182°C.) and the filtrate washed with 3 × 25 ml. water, 1 × 25 ml. saturated sodium chloride solution, and solvent stripped in vacuo to a pale yellow, viscous oil (8.7 g.). Crystallization of the oily product from benzene/hexane in the cold affords 4.2 g of the norbornadiene/2-cyanoacrylic acid adduct, white cyrstals, m.p. 83°-86°C. Another 3.0 g. of adduct, m.p. 81°-84°C., is obtained on concentration of the mother liquors and cooling. The combined crops of adduct are recrystallized from 1:2 benzene/hexane to afford 5.9 g of pure adduct, white crystals, m.p. 81°-83°C. Anal: Neutralization Equivalent: Found, 189.06 g/equiv.; Calculated (Theory), 189.22 g/equiv.

Workup

  1. customInto a flask fitted with a condenser and magnetic stirring bar
  2. temperatureAfter heating
  3. temperatureat reflux for 1.5 hours
  4. extractionextracted with 2 × 25 ml
  5. customof hexane to remove any nonsaponified adduct
  6. filtrationThe extract is filtered
  7. customto remove some white insoluble solids (0. 9g., m.p. 182°C.)
  8. washthe filtrate washed with 3 × 25 ml
  9. customCrystallization of the oily product from benzene/hexane in the

Sources & evidence

ORD record
ord-07abd9e7c39f43e5a4107c68037c602f
Source dataset
uspto-grants-1976_08
Patent number
US03975422

Reaction notes

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