Propargyl alcohol → trans-2-Dodecen-1-ol

HRID 1612803Notes

Reaction equation

HRID 1612803 reaction equation
C(O)C#C.[CH2:5]([OH:17])[C:6]#[C:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>CCOCC.COCCO[AlH2-]OCCOC.[Na+]>[CH2:5]([OH:17])/[CH:6]=[CH:7]/[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 1712322Dodec-2-yn-1-ol

Product 1

HCID 5352845trans-2-Dodecen-1-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 16684438Red-AlSolvent

Procedure

trans-2-Dodecen-1-ol was prepared by reduction of the propargyl alcohol by the method described by Jones and Denmark (Org. Syn., 1985, 64, 182-8) using 6.0 g (33 mmole) of 2-dodecyn-1-ol in 25 ml of ether and 16.2 ml of Red-Al in 30 ml of ether. Kugelrohr distillation afforded 5.73 g of a clear oil. 1H NMR δ5.66 (m, 2), 4.07 (d, 2, J=4 Hz), 2.03 (dd, 2, J=6, 13 Hz), 1.62 (br, 1), 1.4-1.2 (m, 14), 0.88 (t, 3, J=7 Hz).

Workup

  1. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-7fc308628ab34ed19cbef818ff30187c
Source dataset
uspto-grants-1993_03
Patent number
US05190969

Reaction notes

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