Benzene → HCID 53638274, compound

HRID 652832Notes

Reaction equation

HRID 652832 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=O.[O:13]1CCN(C2CCCCC=2)CC1.Cl.[CH:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[O:13]=[C:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C:27]1=[CH:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][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 113441872-(4-formylphenyl)acetic Acid

Product 1

HCID 53638274HCID 53638274, compoundYield 51.2%

Procedure

A solution of 3.28 g (0.02 mole) of p-formylphenylacetic acid and 10.1 g (0.056 mole) of 1-morpholinocyclohexene in 40 ml of benzene was stirred at room temperature for 12 hours, after which 20 ml of 6N hydrochloric acid were added thereto. The mixture was then stirred at room temperature for a further 1 hour, after which it was extracted with diethyl ether. The extract was washed with water and dried over anhydrous sodium sulfate, and the solvent was removed to afford an oily substance, which was purified by silica gel chromatography, eluted with a 1:1 by volume mixture of hexane and ethyl acetate, to give 2.5 g (yield 51.2%) of the title compound as a colorless oily substance.

Workup

  1. extractionafter which it was extracted with diethyl ether
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customto afford an oily substance, which
  6. customwas purified by silica gel chromatography
  7. washeluted with a 1:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-b2f04175b0304279ae2530beb90ece7c
Source dataset
uspto-grants-1987_06
Patent number
US04673761

Reaction notes

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