Methanol → Methyl 12-hydroxydodecanoate

HRID 467387

Reaction equation

HRID 467387 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

HCID 522424Methyl 12-hydroxydodecanoateYield 88%

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-20683f41f6364784950e5d77b96fc046
Source dataset
uspto-grants-2014_01
Patent number
US08623326B2

Linked notes

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