Triacetoxyperiodinane → 16-Ketostearic acid

HRID 1841869Notes

Reaction equation

[OH:1][CH:2]([CH2:20][CH3:21])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>>[O:1]=[C:2]([CH2:20][CH3:21])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

Reactant 2

HCID 159087Triacetoxyperiodinane

HCID 36194316-hydroxy stearic acid

Product 1

HCID 18901616-Ketostearic acid

Procedure

16-hydroxystearic acid was selectively oxidized with Dess-Martin reagent to yield 16-oxostearic acid. The crude product was purified by chromatography using silica gel as separating agent.

Sources & evidence

ORD record: ord-e1c48d6ba812406c9fb07921d79de211
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08945897B2

Reaction notes

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