Hydrochloric Acid → 10,12-Tricosadiynoic Acid

HRID 2106976

Reaktionsgleichung

Reaktionsgleichung von HRID 2106976
[C:1]([OH:13])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11].[OH-].[K+].Cl.NO.I[C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].Cl>O.C(N)C.CO>[C:1]([OH:13])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[C:11][C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 3103910-Undecynoic acidHCID 443297Hydroxyamine hydrochlorideHCID 136005871-Iodododec-1-yne

Produkt 1

HCID 53845710,12-Tricosadiynoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6341EthylamineLösungsmittel

Versuchsvorschrift

10-Undecynoic acid (21.8 g, 0.120 mol) was neutralized with a solution of 57 mL 10 percent KOH in water and hydroxylamine hydrochloride (0.380 g) was added. Then a catalyst consisting of a solution of 1.9 g cuprous chloride in 16 g 70 percent aqueous ethylamine was added. A yellow precipitate formed immediately. A solution of the crude 1-iodo-1-dodecyne in 40 mL methanol was then added dropwise with stirring. The suspension was stirred for one hour after the addition. The reaction mixture was acidified by the addition of 2.5N HCl, filtered, and the filtrate and precipitate washed with ether. The ether layers were washed with water, thiosulfate solution, water and saturated sodium chloride. After drying Na2SO4) the solvents were removed under reduced pressure. The residue was induced to crystallize by scratching under petroleum ether. The crystals of the diyne acid (26.4 g, 74%) exhibited m.p. 57°-58° after recrystallization from acetonitrile.

Aufarbeitung

  1. additionwas added
  2. additionwas added
  3. customA yellow precipitate formed immediately
  4. stirringThe suspension was stirred for one hour
  5. additionafter the addition
  6. filtrationfiltered
  7. washthe filtrate and precipitate washed with ether
  8. washThe ether layers were washed with water, thiosulfate solution, water and saturated sodium chloride
  9. dry with materialAfter drying Na2SO4) the solvents
  10. customwere removed under reduced pressure
  11. customto crystallize
  12. customafter recrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-dea00503b4b24f5ab3f03420aaf878fd
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04933114

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