10-Hydroxydec-6-yn-2-one → HCID 12893740, compound
Reaction equation
[O:1]=[C:2]([CH3:12])[CH2:3][CH2:4][CH2:5][C:6]#[C:7][CH2:8][CH2:9][CH2:10][OH:11].CC(C)=[O:15].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[O:1]=[C:2]([CH3:12])[CH2:3][CH2:4][CH2:5][C:6]#[C:7][CH2:8][CH2:9][C:10]([OH:15])=[O:11]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
20 Grams of 9-oxodec-4-yn-1-ol of Example 16 is dissolved in 200 ml of acetone and cooled to 0° C. The cold solution is stirred and treated dropwise with 90 ml of 2.67 molar Jones reagent (chromic acid in sulfuric acid and water). The acetone solution is decanted from the solid chromium salts, which are then rinsed with fresh acetone. The acetone solutions are combined and poured into a mixture of ether and water. The ether layer is separated from the water, washed once with water, and then extracted three times with 5% potassium carbonate solution. The alkaline extracts are combined, acidified with concentrated hydrochloric acid and extracted twice with ether and once with ethyl acetate. The extracts are combined, dried over sodium sulfate, and stripped of solvent to give the pure title product.
Workup
- customThe acetone solution is decanted from the solid chromium salts, which
- washare then rinsed with fresh acetone
- additionpoured into a mixture of ether and water
- customThe ether layer is separated from the water
- washwashed once with water
- extractionextracted three times with 5% potassium carbonate solution
- extractionextracted twice with ether and once with ethyl acetate
- dry with materialdried over sodium sulfate
Sources & evidence
- ORD record
- ord-22004408a0b049afad19c292a9b8cb40
- Source dataset
- uspto-grants-1982_01
- Patent number
- US04312994
Reaction notes
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