Hydrochloric Acid → HCID 67065110, compound

HRID 2045759Notes

Reaction equation

HRID 2045759 reaction equation
[C:1]([C:3](=[C:8]1[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][CH:9]1[CH3:15])C(OC)=O)#[N:2].[Cl-].[Li+].CN1CCCC1=O.Cl>O>[CH3:14][C:11]1([CH3:13])[CH2:10][CH:9]([CH3:15])[C:8]([CH2:3][C:1]#[N:2])=[CH:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 433294Lithium ChlorideHCID 68226704HCID 68226704, compound

Product 1

HCID 67065110HCID 67065110, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

The methyl 2-cyano-2-(2,4,4-trimethylcyclopentylidene)acetate B is placed in a round-bottomed flask with 2 eq. of lithium chloride in a 98:2 mixture of NMP (N-methylpyrrolidone) and water. The mixture is stirred at 150° C. After 3 hours, the reaction medium is cooled to ambient temperature before being poured onto a 1% HCl solution. Stirring is carried out for a few minutes and then extraction is carried out twice with MTBE (methyl tert-butyl ether). The combined organic phases are washed with a sodium bicarbonate solution and then with an aqueous sodium chloride solution. After drying over magnesium sulfate, filtering through paper and evaporating the solvent, the crude product is distilled under reduced pressure. A 70:30 mixture of 2-(2,4,4-trimethylcyclopent-1-enyl)acetonitrile and 2-(3,3,5-trimethylcyclopent-1-enyl)-acetonitrile is obtained.

Workup

  1. temperaturethe reaction medium is cooled to ambient temperature
  2. stirringStirring
  3. waitis carried out for a few minutes
  4. extractionextraction
  5. washThe combined organic phases are washed with a sodium bicarbonate solution
  6. dry with materialAfter drying over magnesium sulfate
  7. filtrationfiltering through paper
  8. customevaporating the solvent
  9. distillationthe crude product is distilled under reduced pressure
  10. additionA 70:30 mixture of 2-(2,4,4-trimethylcyclopent-1-enyl)acetonitrile

Sources & evidence

ORD record
ord-9eb97fa952594d489f2d082c76f62ec8
Source dataset
uspto-grants-2013_11
Patent number
US08592360B2

Reaction notes

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