16-Bromohexadecanoic acid → 16-Bromo-1-hexadecanol

HRID 130289

Reaktionsgleichung

Reaktionsgleichung von HRID 130289
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18]>C1COCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18]

Komponenten

3

Edukt 1

HCID 62039716-Bromohexadecanoic acid

Produkt 1

HCID 275701316-Bromo-1-hexadecanolAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Under inert atmosphere 10 ml of BH3□THF complex (1.0 M THF solution) were added to 30 ml THF solution of 2.15 gr (6.41 mmole) of 16-bromohexadecanoic acid at −20° C. Reaction mixture was stirred at this temperature for 2 hrs and then additional 1 hr at RT. After that time the resulted mixture was poured, with stirring, into a vessel containing 200 ml of ice/saturated sodium bicarbonate aqueous solution. Organic compounds were extracted with 3×200 ml of ether. The ether fractions were combined and dried over sodium sulfate. After removal of ether material was dissolved in minimum amount of dicloromethane and purified by silica gel chromatography (100% dicloromethane as eluent). 1.92 gr (93% yield) of the desired product were obtained.

Aufarbeitung

  1. customReaction mixture
  2. customadditional 1 hr
  3. customat RT
  4. additionAfter that time the resulted mixture was poured
  5. stirringwith stirring, into a vessel
  6. extractionOrganic compounds were extracted with 3×200 ml of ether
  7. dry with materialdried over sodium sulfate
  8. customAfter removal of ether material
  9. dissolutionwas dissolved in minimum amount of dicloromethane
  10. custompurified by silica gel chromatography (100% dicloromethane as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-02e27c94c13748858721c18abbb505c9
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381533B2

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