3-Decynoic acid → Dec-3-enoic acid
Reaction equation
[C:1]([OH:12])(=[O:11])[CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>CO.B#[Ni]>[C:1]([OH:12])(=[O:11])[CH2:2][CH:3]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To 4.5g (27 mmol) of 3-decynoic acid from Example 30 dissolved in methanol in a Paar bottle is added 2mg of nickel boride as catalyst. The bottle is flushed with hydrogen, sealed and pressurized with H2 at 2 pounds per square inch. The hydrogenation is allowed to proceed at room temperature for 2 hours. The methanol is stripped in vacuo and the residue is partitioned between ethyl acetate and in HCl. The ethyl acetate layer is separated, dried, (Na2SO4) and is stripped to afford an almost quantitative yield of 3-decenoic acid.
Workup
- customThe bottle is flushed with hydrogen
- customsealed
- customthe residue is partitioned between ethyl acetate and in HCl
- customThe ethyl acetate layer is separated
- customdried
Sources & evidence
- ORD record
- ord-2885de98c4634b7dbdfdcc93533fb1ba
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04855324
Reaction notes
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