Hydrochloric Acid → HCID 86641237, compound

HRID 1877337Notes

Reaction equation

HRID 1877337 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[CH3:8].C[O-:10].[K+].[C:12](#[N:22])[CH2:13][CH2:14][CH2:15]CCCCCC.Cl>O.C(OCC)(=O)C>[C:14]([CH:13]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:12]#[N:22])(=[O:10])[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7237O-XyleneHCID 74791DecanenitrileHCID 23664618Potassium methoxide

Product 1

HCID 86641237HCID 86641237, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

In a stirred vessel fitted with reflux condenser and dropping funnel, 317 g of o-xylene were initially charged, 198.96 g of solid potassium methoxide were added and the mixture was heated at reflux. A mixture of 170 g of decanonitrile and 133.9 g of ethyl acetate was then added via the dropping funnel over a period of 10 min. After the addition had ended, stirring was continued for 4 h, and the mixture was then cooled to 105° C. 372 g of water were then added, and the mixture was adjusted to pH 4.3 by addition of about 470 g of 20% strength hydrochloric acid. The temperature was set to 65° C., and the (lower) aqueous phase was removed. The organic phase was washed with another 186 g of water. After removal of the aqueous phase, the organic phase was concentrated to about half of its original volume to remove the water. This gave 211.7 g of a light-yellow solution having a content of product of value of 66.8% a/a (GC), which solution can be reacted further as such. For purification, the compound was distilled under high vacuum, with the product passing over at 106 to 121° C./1 mbar.

Workup

  1. customIn a stirred vessel fitted
  2. temperaturewith reflux condenser
  3. temperaturethe mixture was heated
  4. temperatureat reflux
  5. additionwas then added via the dropping funnel over a period of 10 min
  6. additionAfter the addition
  7. customwas set to 65° C.
  8. customthe (lower) aqueous phase was removed
  9. washThe organic phase was washed with another 186 g of water
  10. customAfter removal of the aqueous phase
  11. concentrationthe organic phase was concentrated to about half of its original volume
  12. customto remove the water
  13. customcan be reacted further as such
  14. customFor purification
  15. distillationthe compound was distilled under high vacuum, with the product
  16. custompassing over at 106 to 121° C./1 mbar

Sources & evidence

ORD record
ord-44825d8596214952bbc8a51e1a874afa
Source dataset
uspto-grants-2012_11
Patent number
US08309751B2

Reaction notes

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