Acetic Acid → HCID 86735614, compound

HRID 903329Notes

Reaction equation

HRID 903329 reaction equation
[Na].[CH2:2]([C:9]([CH3:11])=[O:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:12](O)(=O)[CH3:13]>CO>[C:3]1([CH:2]([C:9](=[O:10])[CH2:11][CH2:9][CH2:2][CH2:3][CH2:4][CH2:12][CH3:13])[CH2:5][CH2:6][CH3:7])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7678PhenylacetoneHCID 5360545Sodium

Product 1

HCID 86735614HCID 86735614, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution prepared from 3 g sodium metal in 100 ml absolute methanol there was added 45 g methyl benzyl ketone. The resulting solution was refluxed for 30 minutes, cooled to 0° C. and 39 g 2-methylene-3-quinolidinone was added. The solution was stirred at ambient temperature during 48 hours, netralized by the addition of 3 ml acetic acid and the solvents were removed under reduced pressure. There was obtained a crude oil which was extracted with chloroform. After evaporation of the solvent there was obtained 52 g (a yield of 60%) of the desired product, M.P. from acetone, 125.7° C. Treatment with hydrochloric acid gave the corresponding hydrochloride salt, M.P. above 300° C. (dec.).

Workup

  1. temperatureThe resulting solution was refluxed for 30 minutes
  2. addition39 g 2-methylene-3-quinolidinone was added
  3. customthe solvents were removed under reduced pressure
  4. customThere was obtained a crude oil which
  5. extractionwas extracted with chloroform
  6. customAfter evaporation of the solvent there

Sources & evidence

ORD record
ord-49b25d917c3147c0ac8f855643996f47
Source dataset
uspto-grants-1980_10
Patent number
US04226996

Reaction notes

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