Stearic Acid → (+)-Vernolic acid

HRID 260936Notes

Reaction equation

HRID 260936 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].C(O)(=[O:39])CCCCCCCCCCCCCCCCC>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[O:39][C@H:7]1[CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

3

Reactant 2

HCID 5281Stearic AcidHCID 5280450Linoleic Acid

Product 1

HCID 6449780(+)-Vernolic acid

Procedure

Vernolia oil undergoes saponification and acification followed by cold temperature (-20° C.) crystallization to yield a methylated product comprised of vernolic, palmitic, oleic, linoleic and stearic acid. The vernolic acid is isolated and further purified through a series of low temperature recrystalizations. The purified vernolic acid, ##STR1## is then hydrogenated to yield 12,13-epoxystearic acid, having the formula: ##STR2## The 12,13-epoxystearic acid is then oxidized to yield 12-oxododecanoic acid, ##STR3## By reacting the 12-oxododecanoic acid with hydroxylamine, 12-oxododecanoic acid oxime ##STR4## is formed. The Nylon-12 monomer, 12-aminododecanoic acid:

Workup

  1. customfollowed by cold temperature (-20° C.) crystallization
  2. customto yield a methylated product

Sources & evidence

ORD record
ord-802c3cf9329a44dc8cd919d03efdded8
Source dataset
uspto-grants-1996_06
Patent number
US05530148

Reaction notes

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