11-DODECYN-1-OL Chemical Properties

Melting point:

18.8°C (estimate)

Boiling point:

285.73°C (rough estimate)

Density 

0.8530 (estimate)

refractive index 

1.4535 (estimate)

storage temp. 

2-8°C

form 

<26°C Solid,>28°C Liquid

pka

15.20±0.10(Predicted)

color 

Colorless to off-white

InChI

InChI=1S/C12H22O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h1,13H,3-12H2

InChIKey

XNRAUTMOUDUPET-UHFFFAOYSA-N

SMILES

C(O)CCCCCCCCCC#C

11-DODECYN-1-OL Usage And Synthesis

Uses

11-Dodecyn-1-ol is a synthetic intermediate of the sex pheromone (Z,E)-11,13,15-Hexadecatrienyl acetate for Thaumetopoea processionea[1].

Synthesis

NaH (7.5 g, 60% oil dispersion, 326 mmol) was added batchwise to a stirred 0 ??C solution of dodeca-3-yn-1-ol (10.0 g, 54.95 mmol; GF Smith) in ethylenediamine (40 mL).After 1 h, the temperature was raised to 70 ??C. The reaction mixture was cooled to 0 ??C for another 8 h and carefully terminated with ice-cold water (100 mL) and extracted with ether (3 x 60 mL). After another 8h, the reaction mixture was cooled to 0 ??C, carefully terminated with ice-cold water (100 mL) and extracted with ether (3 x 60 mL). The combined ether extracts were washed with water (100 mL). The aqueous washings were back-extracted with ether (3 x 60mL). The combined organic extracts were concentrated under vacuum and the residue was subjected to column chromatography using 10% EtOAc/hexane to obtain 11-dodecyne-1-ol (7.4 g, 74%) contaminated with 3-5% of other regioisomers (regioisomer).TLC: 30% EtOAc/hexane, Rf ?? 0.4; 1H NMR (300 MHz, CDCl3). CDCl3) ?? 3.66 (t, 2H, J = 7.3 Hz), 2.14-2.21 (m, 2H), 1.93 (t, J = 1.9 Hz, 1H), 1.20-1.63 (m, 16H).

References

[1] Gries R, et al. (Z, Z)-11, 13-Hexadecadienyl acetate and (Z, E)-11, 13, 15-hexadecatrienyl acetate: synergistic sex pheromone components of oak processionary moth, Thaumetopoea processionea (Lepidoptera: Thaumetopoeidae)[J]. Chemoecology, 2004, 14: 95-100...

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