Thioglycerol → (+/-)-1-S-hexadecylthioglycerol

HRID 977278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 977278
[SH:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[OH-].[K+].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(O)C>[CH2:25]([S:1][CH2:2][CH:3]([CH2:4][OH:5])[OH:6])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10]

Komponenten

5

Edukt 3

HCID 7291ThioglycerolHCID 82131-BromohexadecaneHCID 14797Potassium Hydroxide

Produkt 1

HCID 13002863(+/-)-1-S-hexadecylthioglycerolAusbeute 950,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 40.0 grams (0.037 mole) 3-mercapto-1,2-propanediol in 300 milliliters of 95% ethanol, 24.9 grams (0.44 mole) of KOH was added under an inert atmosphere of nitrogen. Then, a solution of 135.0 grams (0.44 mole) bromohexadecane in 100 milliliters of 95% ethanol was added dropwise over a one-hour period, and the reaction allowed to proceed at room temperature with vigorous stirring for 24 hours. The precipitate was filtered, taken up in one liter of boiling methanol and cooled to 0° Centigrade for twelve hours. The precipitate was filtered and allowed to air dry, producing 117 grams (95%) of product (mp 72°-74° Centigrade).

Aufarbeitung

  1. customto proceed at room temperature
  2. filtrationThe precipitate was filtered
  3. temperaturecooled to 0° Centigrade for twelve hours
  4. filtrationThe precipitate was filtered
  5. customto air dry

Quellen und Nachweise

ORD-Eintrag
ord-2f81c92e4dc44e7cb7e04f2b12e41f15
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614548

Notizen zur Reaktion

Wird geladen…