Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 17-Acetoxy-heptadecanol

HRID 1367717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367717
[C:1]([O: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][CH2:18][CH2:19][CH2:20][CH2:21][O:22]C1CCCCO1)(=[O:3])[CH3:2].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CCO.CCOC(C)=O>[C:1]([O: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][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57548717Tetrahydro-2-(17-acetoxyheptadecyloxy)-2H-pyran

Produkt 1

HCID 8662564017-Acetoxy-heptadecanolAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

THP ether 39 (1.207 g, 3.03 mmol) was dissolved in 95% EtOH (12 ml) and PPTS (76 mg, 0.3 mmol) was added. The mixture was stirred at 55° C. for 4 h, cooled to room temperature and diluted with EtOAc. This mixture was washed with H2O three times, the organic phase was dried over Na2SO4 and evaporated. The residue was chromatographed on silica gel to give 864 mg (91%) of 17-acetoxy-heptadecanol.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. washThis mixture was washed with H2O three times
  3. dry with materialthe organic phase was dried over Na2SO4
  4. customevaporated
  5. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f7d378f1090b4ac0b2262fb162384bb9
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893286B2

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