Palmitic Acid → 2-Hydroxydecanoic Acid

HRID 2071434Notes

Reaction equation

HRID 2071434 reaction equation
Br[CH:2]([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][CH3:19])[C:3]([OH:5])=[O:4].[C:20](O)(=[O:36])CCCCCCCCCCCCCCC.[OH-].[K+].[OH:40][CH:41]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]CCCCCC)[C:42]([OH:44])=[O:43]>CO.[N+](=C)=[N-]>[CH3:20][O:36][CH:2]([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][CH3:19])[C:3]([O:5][CH3:41])=[O:4].[OH:40][CH:41]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C:42]([OH:44])=[O:43]

Participants

8

Reactant 4

HCID 985Palmitic AcidHCID 14797Potassium HydroxideHCID 821452-Bromohexadecanoic acidHCID 928362-Hydroxyhexadecanoic acid

Product 2

HCID 214882-Hydroxydecanoic AcidHCID 617760Methyl 2-methoxyhexadecanoate

Reagents, catalysts & solvents 2

HCID 9550DiazomethaneCatalystHCID 887MethanolSolvent

Procedure

2-Bromohexadecanoic acid (m.p. 51.5°-52.5° C) prepared from palmitic acid of high purity according to the method of Schwenk, E. and Papa, D; J. Am. Chem. Soc., 70 (1948) 3626, was treated with a solution of potassium hydroxide in 95 % methanol in an oil bath at 90° C at which 2-hydroxyhexadecanoic acid (m.p. 86.1°-86.3° C after recrystallization from ethanol and then from dichloromethane) was formed. Methyl 2-methoxyhexadecanoate (m.p. 28.6°-30.6° C) was obtained from 2-hydroxydecanoic acid by esterification and etherification with diazomethane using borone trifluoride as catalyst for the esterification whereafter it was reduced with lithium aluminum hydride to the formation of 2-methoxyhexadecanol-1 (m.p. 34.3°-34.9° C) which was purified by chromatography on silicic acid, 2-methoxyhexadecyl p-toluenesulphonate (m.p. 38°-39° C) was prepared by treating 2-methoxyhexadecanol with p-toluenesulphonylchloride in pyridine.

Workup

  1. customafter recrystallization from ethanol
  2. customfrom dichloromethane) was formed

Sources & evidence

ORD record
ord-14ad0d92e7274c0382deae015c4140f9
Source dataset
uspto-grants-1977_09
Patent number
US04046914

Reaction notes

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