Acetic Acid → HCID 86735614, compound

HRID 1105664Notes

Reaction equation

HRID 1105664 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.[CH2:12]=[C:13]1[C:18](=O)[CH:17]2[CH2:20][CH2:21]N1CC2.[C:22](O)(=O)[CH3:23].[CH3:26]O>>[C:3]1([CH:2]([C:9](=[O:10])[CH2:11][CH2:21][CH2:20][CH2:17][CH2:18][CH2:13][CH3:12])[CH2:26][CH2:22][CH3:23])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 7678PhenylacetoneHCID 3229732-Methylene-3-quinuclidoneHCID 5360545Sodium

Product 1

HCID 86735614HCID 86735614, compoundYield 60%

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-quinuclidinone was added. The solution was stirred at ambient temperature during 48 hours, neutralized 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. customthe solvents were removed under reduced pressure
  3. customThere was obtained a crude oil which
  4. extractionwas extracted with chloroform
  5. customAfter evaporation of the solvent there

Sources & evidence

ORD record
ord-74b7739d725f4c9e9fd638a9d75b87ff
Source dataset
uspto-grants-1982_01
Patent number
US04309544

Reaction notes

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