Water → 1-Nonyn-4-one

HRID 1106295Notes

Reaction equation

HRID 1106295 reaction equation
[CH:1]#[C:2][CH2:3][CH:4]([OH:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.CCCCCC.O>CC(C)=O>[CH:1]#[C:2][CH2:3][C:4](=[O:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 109863221-Nonyn-4-olHCID 131709961Jones' reagent

Product 1

HCID 205539671-Nonyn-4-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 14 g of 1-nonyn-4-ol in 100 ml of acetone is cooled to 0° and treated dropwise with 70 ml of 2.67 molar Jones reagent with stirring. The reaction mixture is poured into a mixture of hexane and water, the organic layer is separated and washed with water, dried over sodium sulfate, stripped of solvent, and the residue distilled to give the title product.

Workup

  1. customthe organic layer is separated
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. distillationthe residue distilled

Sources & evidence

ORD record
ord-fdf6124e36594f11b8fdd3d79d68d91a
Source dataset
uspto-grants-1982_01
Patent number
US04312994

Reaction notes

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