9-Dodecyn-1-ol → Dodec-11-yn-1-ol

HRID 398220Notes

Reaction equation

HRID 398220 reaction equation
C(O)CCCCCCC#C.[CH2:11]([OH:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]#[C:20][CH2:21][CH3:22]>NCCCN>[CH2:11]([OH:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[CH:22]

Participants

4

Reactant 2

HCID 1170119-Dodecyn-1-olHCID 38061428-Nonyn-1-ol

Product 1

HCID 10943108Dodec-11-yn-1-ol

Reagents, catalysts & solvents 1

HCID 4281,3-PropanediamineSolvent

Procedure

The same procedure for 8-nonyn-1-ol was followed with 9-dodecyn-1-ol (4.68 g, 25.7 mmol), KH(3.09 g, 77.0 mmol), and 1,3-diaminopropane (70 mL). This produced 4.33 g of yellow oil (93%): IR (neat) ν 3317,2930, 2121 cm−1; 1H—NMR δ 3.62 (t, 2H, J=6.6 Hz), 2.17 (td, 2H, J=2.6 Hz, 7.1 Hz), 1.93 (t, 1H, J=2.6 Hz), 1.76 (bs, 1H), 1.55 (m, 4H), 1.28 bm, 12H); 13C—NMR δ 84.8, 68.0, 63.0, 32.7, 29.5, 29.4 (2C), 29.0, 28.7, 28.4, 25.7, 18.4; MS m/z 189.18 (M++Li).

Sources & evidence

ORD record
ord-2a0f672010a6413f84e5a08345ff3398
Source dataset
uspto-grants-2003_08
Patent number
US06610835B1

Reaction notes

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