Pentadeca-8,14-diyn-1-ol → Pentadeca-8,14-diynoic acid

HRID 918975Notes

Reaction equation

HRID 918975 reaction equation
[CH2:1]([OH:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[CH:15].CC(C)=[O:19].OS(O)(=O)=O.O=[Cr](=O)=O>>[C:1]([OH:19])(=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[CH:15]

Participants

3

Reactant 2

HCID 86665264Pentadeca-8,14-diyn-1-olHCID 131709961Jones' reagent

Product 1

HCID 87394290Pentadeca-8,14-diynoic acidYield 87%

Procedure

Oxidation of pentadeca-8,14-diyn-1-ol (3.0 g, 13.69 mmol) using Jones reagent as described above and purification by SiO2 column chromatography using 15% EtOAc/hexanes as eluent gave pentadeca-8,14-diynoic acid (2.80 g, 87%) as a colorless oil. TLC: 30% EtOAc/hexanes, Rf≈0.33; 1H NMR (400 MHz, CDCl3) δ 2.34 (t, J=7.0 Hz, 2H), 2.10-2.18 (m, 6H), 1.93 (t, J=2.6 Hz, 1H), 1.55-1.67 (m, 6H), 1.33-1.49 (m, 6H).

Workup

  1. custompurification by SiO2 column chromatography

Sources & evidence

ORD record
ord-d70263b5d7d24e80a4d0d75616724aea
Source dataset
uspto-grants-2016_03
Patent number
US09272991B2

Reaction notes

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