Sulfuric Acid → 11-bromoundec-10-ynoic Acid

HRID 485292

Reaktionsgleichung

Reaktionsgleichung von HRID 485292
[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].[Br:14][O-].[Na+].Br[O-].BrBr.OS(O)(=O)=O>[OH-].[Na+]>[Br:14][C:11]#[C:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:13])=[O:12]

Komponenten

7

Edukt 5

HCID 1118Sulfuric AcidHCID 24408BromineHCID 3103910-Undecynoic acidHCID 5460626HypobromiteHCID 23673712Sodium hypobromite

Produkt 1

HCID 411287611-bromoundec-10-ynoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel2×

Versuchsvorschrift

To a solution of 36.45 g (200 mmol) of 10-undecynoic acid in 200 ml 1N NaOH at 0° C. was added a solution of alkaline sodium hypobromite dropwise over 30 minutes, maintaining the temperature below 5° C. (the hypobromite solution was prepared by the dropwise addition of 35.16 g (220 mmol) of bromine to 55 ml of 20N NaOH at 0°-5° C.). The mixture was stirred four hours at 0°-5° C., and was then acidified to pH 1 with 9M H2SO4. The solution was extracted with three 150 ml portions of ether. The combined extracts were dried (Na2SO4) and evaporated yielding 50.159 (96% crude) of a pale yellow solid. This was used without further purification.

Aufarbeitung

  1. extractionThe solution was extracted with three 150 ml portions of ether
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customevaporated
  4. customyielding 50.159 (96% crude) of a pale yellow solid
  5. customThis was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d7cb6e6fbdc8408b8fd13af33f73c559
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04536450

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