p-Toluenesulfonic acid → Methyl 16-(2-tetrahydropyranyloxy)hexadecanoate

HRID 2258144

Reaktionsgleichung

[OH: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:19][CH3:20])=[O:18].[C:21]1(C)C=[CH:25][C:24](S(O)(=O)=O)=[CH:23][CH:22]=1.C([O-])(O)=[O:33].[Na+]>ClCCl>[O:33]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O: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:19][CH3:20])=[O:18]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

100.26 g (0.35 mol) of methyl 16-hydroxyhexadecanoate, 0.60 g (3.5 mol) of p-toluenesulfonic acid and 350 ml of dichloromethane were introduced into a 1-1 flask equipped with a stirrer and a dropping funnel and 32.39 g (0.385 mol) of dihydropyan was dropped thereto under stirring at 0° C. After the completion of the addition, the mixture was stirred at room temperature for additional 1 hour to thereby complete the reaction. Next, the reaction mixture was neutralized by adding 0.59 g (7 mmol) of NaHCO3 and filtered. After distilling off the solvent, crude methyl 16-(2-tetrahydropyranyloxy)hexadecanoate (III-a) was obtained.

Aufarbeitung

customequipped with a stirrer and a dropping funnel
addition32.39 g (0.385 mol) of dihydropyan was dropped
additionAfter the completion of the addition
stirringthe mixture was stirred at room temperature for additional 1 hour
customthe reaction
filtrationfiltered
distillationAfter distilling off the solvent

Quellen und Nachweise

ORD-Eintrag: ord-b52d24b078eb4fa2883462d1a856be8a
Quelldatensatz: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05659052

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