Potassium Hydroxide → 3-(4-Biphenylyl)-2-butenoic acid

HRID 67138Notes

Reaction equation

HRID 67138 reaction equation
C([O:3][C:4](=[O:20])[CH:5]=[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH3:7])C.[OH-].[K+]>C(O)C>[C:11]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:12]=[CH:13][C:8]([C:6]([CH3:7])=[CH:5][C:4]([OH:20])=[O:3])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 545016723-(4-Biphenylyl)-2-butenoic acid ethyl ester

Product 1

HCID 2967533-(4-Biphenylyl)-2-butenoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product resulting from (a), above, is mixed with 6 g of 85% potassium hydroxide in 100 ml of aqueous ethanol and the resulting mixture heated on a steam bath for 30 minutes. The mixture is then cooled, poured into ice and extracted thrice with 25 ml portions of diethylether. The aqueous phase is filtered over Celite and the filtrate acidified with 2 N hydrochloric acid to pH 4 and cooled. The resulting precipitate is filtered, washed with ether, air dried with suction and then dried under high vacuum at 50° C. to yield the heading compound, substantially in trans form.

Workup

  1. temperaturethe resulting mixture heated on a steam bath for 30 minutes
  2. temperatureThe mixture is then cooled
  3. additionpoured into ice
  4. extractionextracted thrice with 25 ml portions of diethylether
  5. filtrationThe aqueous phase is filtered over Celite
  6. temperaturecooled
  7. filtrationThe resulting precipitate is filtered
  8. washwashed with ether, air
  9. customdried with suction
  10. customdried under high vacuum at 50° C.
  11. customto yield the heading compound

Sources & evidence

ORD record
ord-adad65625ed443a585f437e7219331b8
Source dataset
uspto-grants-1982_08
Patent number
US04344966

Reaction notes

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