Docos-21-yn-1-ol → Docos-21-ynoic Acid

HRID 2399982Notes

Reaction equation

HRID 2399982 reaction equation
[CH2:1]([OH:23])[CH2:2][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][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[CH:22].CC(C)=[O:26].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:1]([OH:26])(=[O:23])[CH2:2][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][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[CH:22]

Participants

4

Reactant 2

HCID 57307871Docos-21-yn-1-olHCID 131709961Jones' reagent2×

Product 1

HCID 54502951Docos-21-ynoic AcidYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Docos-21-ynol (12 g, 0.037 mol) was dissolved in warm acetone (600 ml) treated with Jones reagent (20 ml). After stirring for 30 minutes tlc showed complete reaction so the excess Jones reagent was quenched with propane-2-ol and the volatile components removed in vacuo. The organic fractions were combined, dried (MgSO4), filtered and evaporated to leave docos-21-ynoic acid (32) as a pale green solid (10.4 g, 83%).

Workup

  1. customwas quenched with propane-2-ol
  2. customthe volatile components removed in vacuo
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a634d028ac4e474888d468f3e253aee9
Source dataset
uspto-grants-1995_09
Patent number
US05451691

Reaction notes

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