Methanol → Methyl 12-hydroxydodecanoate

HRID 467387

反応式

HRID 467387 の反応式
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]

参加物

4

反応物 3

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

生成物 1

HCID 522424Methyl 12-hydroxydodecanoate収率 88%

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-20683f41f6364784950e5d77b96fc046
出典データセット
uspto-grants-2014_01
特許番号
US08623326B2

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