Water → 2-Hexadecanoyloxyhexadecanoic acid

HRID 236477

Reaktionsgleichung

Reaktionsgleichung von HRID 236477
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]([OH:5])=[O:4].[C:20](Cl)(=[O:36])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].O>N1C=CC=CC=1>[C:20]([O:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]([OH:5])=[O:4])(=[O:36])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Komponenten

5

Edukt 3

HCID 962WaterHCID 8206Palmitoyl chlorideHCID 928362-Hydroxyhexadecanoic acid

Produkt 1

HCID 133718622-Hexadecanoyloxyhexadecanoic acidAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

α-Hydroxypalmitic acid (3.2 g) was dissolved in pyridine (15 ml), and palmitoyl chloride (3.3 g) was added thereto at 0° C. The resulting mixture was allowed to stand overnight at room temperature. The reaction mixture was poured into water and the aqueous solution was stirred at room temperature for 1 hour, followed by acidification with 1N hydrochloric acid, and extraction with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated to give a residue which was recrystallized from petroleum ether to afford crystals of 2-hexadecanoyloxyhexadecanoic acid (5.4 g). M.p. 55°-56° C.

Aufarbeitung

  1. customat 0° C
  2. extractionfollowed by acidification with 1N hydrochloric acid, and extraction with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas recrystallized from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-0b0c7c1525044b2f92dfe7f214498d11
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04643990

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