4-Acetylbutyric acid → HCID 13839457, compound
Reaction equation
[O:1]=[C:2]([CH3:9])[CH2:3][CH2:4][CH2:5][C:6](O)=[O:7].S(Cl)([Cl:12])=O>>[O:1]=[C:2]([CH3:9])[CH2:3][CH2:4][CH2:5][C:6]([Cl:12])=[O:7]Participants
3
Procedure
As shown in Table B, 5-ketohexanoic acid IX was reacted with thionyl chloride. The reaction mixture yielded 5-ketohexanoylchloride X which was recovered after distillation. The 5-ketohexanoyl chloride X intermediate was reacted with acetylene and aluminum chloride and converted into the chloro-diketone compound XI. The diketone compound was converted into the corresponding iodovinyl diol XIII by adding to the reaction mixture sodium iodide in a solvent such as acetone, and reducing the intermediate compound XII to the diol by adding sodium borohydride.
Sources & evidence
- ORD record
- ord-6586ffb3f6a04ceb90b1bb88d8d0442a
- Source dataset
- uspto-grants-1978_11
- Patent number
- US04127612
Reaction notes
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