3-Decynoic acid → Dec-3-enoic acid

HRID 1722349Notes

Reaction equation

HRID 1722349 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

HCID 5493723-Decynoic acid

Product 1

HCID 85855Dec-3-enoic acid

Reagents, catalysts & solvents 2

HCID 82791nickel boride (NiB)CatalystHCID 887MethanolSolvent

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

  1. customThe bottle is flushed with hydrogen
  2. customsealed
  3. customthe residue is partitioned between ethyl acetate and in HCl
  4. customThe ethyl acetate layer is separated
  5. customdried

Sources & evidence

ORD record
ord-2885de98c4634b7dbdfdcc93533fb1ba
Source dataset
uspto-grants-1989_08
Patent number
US04855324

Reaction notes

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