Hydrochloric Acid → 3-(Hexadecyloxy)-2-(tetradecyloxy)propan-1-OL

HRID 1755968

Reaktionsgleichung

Reaktionsgleichung von HRID 1755968
C(Br)CCCCCCCCCCCCC.[OH-].[K+].C(C(C(CO)O)O)C1C=CC=CC=1.[CH2:31]([O:47][CH2:48][CH:49]([CH2:67][OH:68])[O:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64]CC)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].C(OCC(COC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)OCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC.Cl>C1(C)C=CC=CC=1>[CH2:31]([O:47][CH2:48][CH:49]([CH2:67][OH:68])[O:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 8208Myristyl bromideHCID 14797Potassium HydroxideHCID 1025482,3-Bis(hexadecyloxy)propan-1-olHCID 2735483BenzylglycerolHCID 571290511-Hexadecyl-2-tetradecyl-3-trityl glycerol

Produkt 1

HCID 571281113-(Hexadecyloxy)-2-(tetradecyloxy)propan-1-OL

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

1-hexadecyl glycerol (105 g, 0.33 mol) and 93 g (0.33 mol) tritylchloride were dissolved in 300 ml of pyridine. The mixture was heated at 100° C. for 16 hours. After cooling to room temperature 1500 ml of ethyl ether was added and the slurry washed 3 times with cold 0.5N H2SO4, 5% sodium bicarbonate and 2 times with water. The organic phase was dried over MgSO4, the ether removed on a rotary evaporator and the residue recrystallized from ethanol, yielding the intermediate 1-hexadecyl-3-trityl glycerol (129 g, 70%). The 2 position of this intermediate was alkylated with tetradecyl bromide in the same manner (powdered KOH in toluene) as described earlier for the dialkylation of benzyl glycerol in the preparation of 1,2-dihexadecyl glycerol. The resulting 1-hexadecyl-2-tetradecyl-3-trityl glycerol (128g) was dissolved in 300 ml of petroleum ether. At room temperature 30g of anhydrous hydrogen chloride was added. A precipitate formed within a short time. The slurry was stirred at room temperature for 4 hours and then filtered. The solids were recrystallized from acetone (10° C.) to give 45.6g of product, m.p. 42°-3° C.

Aufarbeitung

  1. customA precipitate formed within a short time
  2. filtrationfiltered
  3. customThe solids were recrystallized from acetone (10° C.)

Quellen und Nachweise

ORD-Eintrag
ord-da3bd6221bbd4f568006381924c4c0bf
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05439669

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