Benzene → 2-[4-(2-Oxocyclohexylidenemethyl)phenyl]propionic acid

HRID 652830Notes

Reaction equation

HRID 652830 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=O.[O:14]1CCN(C2CCCCC=2)CC1.Cl.[CH:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[O:14]=[C:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C:28]1=[CH:1][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 69589Morpholine, 4-(1-cyclohexen-1-yl)-HCID 102196632-(4-Formylphenyl)propionic acid

Product 1

HCID 1296782-[4-(2-Oxocyclohexylidenemethyl)phenyl]propionic acidYield 77.7%

Procedure

A solution of 3.56 g (0.02 mole) of 2-(p-formylphenyl)propionic acid and 10.1 g (0.056 mole) of 1-morpholinocyclohexene in 40 ml of benzene was allowed to stand overnight (12 hours) at room temperature, after which 20 ml of 6N hydrochloric acid were added thereto, and the mixture was stirred for 1 hour at room temperature. The reaction mixture was then extracted with benzene; the extract was washed with water and dried; and the solvent was removed by evaporation under reduced pressure to give a crystalline substance. This was recrystallized from a mixture of diethyl ether and hexane, to give 4.02 g (yield 77.7%) of the title compound as white crystals melting at 108°-110° C.

Workup

  1. extractionThe reaction mixture was then extracted with benzene
  2. washthe extract was washed with water
  3. customdried
  4. customand the solvent was removed by evaporation under reduced pressure
  5. customto give a crystalline substance
  6. customThis was recrystallized from a mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-5ca09a9dbabc4e9eb86c14927b27d320
Source dataset
uspto-grants-1987_06
Patent number
US04673761

Reaction notes

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