Hydrochloric Acid → HCID 86641236, compound

HRID 1887182Notes

Reaction equation

HRID 1887182 reaction equation
[CH3:1][O-:2].[K+].[CH3:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[CH3:11].[C:12](#[N:22])[CH2:13][CH2:14][CH2:15]CCCCCC.Cl.[OH2:24]>C(O)C>[CH3:1][O:2][CH2:15][C:14]([CH:13]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH3:4])[C:12]#[N:22])=[O:24]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 7237O-XyleneHCID 74791DecanenitrileHCID 23664618Potassium methoxide

Product 1

HCID 86641236HCID 86641236, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

In a stirred vessel fitted with reflux condenser and dropping funnel, 199.96 g of solid potassium methoxide were initially charged, and 318 g of o-xylene were added. 15 g of ethanol were added, and the suspension was heated to reflux. A mixture of 170 g of decanonitrile and 180.8 g of ethyl methoxy acetate was then added via the dropping funnel over a period of 10 min. After the addition had ended, stirring was continued for 6 h, and the mixture was then cooled to 105° C. 373 g of water were then added, and the mixture was adjusted to pH 4 by addition of about 388 g of 20% strength hydrochloric acid. The temperature was set to 70° 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 half of its original volume in order to remove the water. This gave 235.5 g of a pale yellow solution having a content of product of value of 62% a/a (GC), which can be reacted further as such. For purification, the compound was distilled under high vacuum, with the product passing over at 120 to 134° C./1 mbar.

Workup

  1. customIn a stirred vessel fitted
  2. temperaturewith reflux condenser
  3. temperaturethe suspension was heated to reflux
  4. additionwas then added via the dropping funnel over a period of 10 min
  5. additionAfter the addition
  6. customwas set to 70° C.
  7. customthe (lower) aqueous phase was removed
  8. washThe organic phase was washed with another 186 g of water
  9. customAfter removal of the aqueous phase
  10. concentrationthe organic phase was concentrated to half of its original volume in order
  11. customto remove the water
  12. customcan be reacted further as such
  13. customFor purification
  14. distillationthe compound was distilled under high vacuum, with the product
  15. custompassing over at 120 to 134° C./1 mbar

Sources & evidence

ORD record
ord-487b22c9305e4e10a2f0c0e5df19980c
Source dataset
uspto-grants-2013_08
Patent number
US08501748B2

Reaction notes

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