Methanol → Methyl 12-hydroxydodecanoate

HRID 467387

Reaktionsgleichung

Reaktionsgleichung von HRID 467387
OS(O)(=O)=O.[O:6]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:19].[CH3:20][OH:21]>>[CH3:20][O:21][C:18](=[O:6])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][OH:19]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 70354Oxacyclotridecan-2-one

Produkt 1

HCID 522424Methyl 12-hydroxydodecanoateAusbeute 88 %

Versuchsvorschrift

Concentrated H2SO4 (0.2 mL) was added to a solution of oxacyclotridecan-2-one (850 mg, 4.3 mmol) in 20 mL of methanol and stirred for 1 day. Methanol was removed under reduced pressure and the aqueous residue was extracted with diethyl ether 3 times. The combined organic layers were washed with saturated NaHCO3, saturated NaCl, and then dried over MgSO4. The diethyl ether was removed under reduced pressure to yield 874 mg (88%) of 14c as a white solid. 1H-NMR (400 MHz, CDCl3, δH ppm): 3.65 (3H, s, CO2CH3), 3.63 (2H, t, 3JH—H=6.6 Hz, HO—CH2), 2.29 (2H, t, 3JH—H=7.6 Hz, CH2CO2), 1.50-1.66 (4H, m, 2CH2), 1.22-1.38 (14H, m, 7CH2). HRMS (EI): m/z calcd 231.1955 ([M+H]+, C13H27O3), found 231.1954 [M+H]+.

Aufarbeitung

  1. customMethanol was removed under reduced pressure
  2. extractionthe aqueous residue was extracted with diethyl ether 3 times
  3. washThe combined organic layers were washed with saturated NaHCO3, saturated NaCl
  4. dry with materialdried over MgSO4
  5. customThe diethyl ether was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-20683f41f6364784950e5d77b96fc046
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623326B2

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