Hydrochloric Acid → 4-Chloro-α-[(3,4-dihydroxyphenyl)methylene]benzeneacetonitrile

HRID 1082254Notes

Reaction equation

HRID 1082254 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[OH:20])[CH:15]=O.N1CCCCC1.Cl>C(O)C>[C:9]([C:8](=[CH:15][C:14]1[CH:17]=[CH:18][C:19]([OH:20])=[C:12]([OH:11])[CH:13]=1)[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)#[N:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 87683,4-DihydroxybenzaldehydeHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 9120154-Chloro-α-[(3,4-dihydroxyphenyl)methylene]benzeneacetonitrileYield 67.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 758 mg (5.00 mmole) of 4-chlorophenylacetonitriie (purchased from Tokyo Kasei), 691 mg (5.00 mmole) of 3,4-dihydroxybenzaldehyde (purchased from Tokyo Kasei) and 10 ml of ethanol (purchased from Kokusan Kagaku) were added 0.54 ml of piperidine (purchased from Wako Junyaku Kogyo), the mixture was refluxed with heating for 6 hours and air-cooled, the reaction product was added to 100 ml of 1N hydrochloric acid, and deposits were filtered, washed with water, dissolved in ethyl acetate, washed with a 20% sodium hydrogensulfite solution twice and subsequently with saturated saline once and dried over sodium anhydrous sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified according to silica gel column chromatography (effluent with a ratio of hexane to ethyl acetate of 5:1 to 5:2 used) to obtain 919 mg (yield: 67.6%) of α-cyano-4-chloro-3',4'-dihydroxystilbene (yellow crystal) represented by the following formula: ##STR147##

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 6 hours
  3. temperatureair-cooled
  4. filtrationwere filtered
  5. washwashed with water
  6. dissolutiondissolved in ethyl acetate
  7. washwashed with a 20% sodium hydrogensulfite solution twice
  8. dry with materialsubsequently with saturated saline once and dried over sodium anhydrous sulfate
  9. distillationThen, the solvent was distilled off under reduced pressure
  10. customthe residue was purified

Sources & evidence

ORD record
ord-64af1e56884b40b7813f971284091416
Source dataset
uspto-grants-1996_12
Patent number
US05589506

Reaction notes

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