Name | Dodec-11-yn-1-ol |
Synonyms | 11-DODECYN-1-OL 11-dodecyn-1-01 odec-11-yn-1-ol Dodec-11-yn-1-ol 11-Dodecyne-1-ol |
CAS | 18202-10-3 |
Molecular Formula | C12H22O |
Molar Mass | 182.3 |
Density | 0.8530 (estimate) |
Melting Point | 18.8°C (estimate) |
Boling Point | 285.73°C (rough estimate) |
pKa | 15.20±0.10(Predicted) |
Storage Condition | 2-8°C |
Refractive Index | 1.4535 (estimate) |
preparation | NaH(7.5g,60% oil dispersion, 326mmol) was added batch by batch to dodecyl -3-alkyne -1-alcohol (10.0g,54.95mmol;GF Smith) in a stirred 0 ℃ solution of ethylenediamine (40mL). After 1h, the temperature was raised to 70 ℃. After another 8h, cool the reaction mixture to 0°C, carefully terminate with ice-cold water (100mL), and extract with ether (3 × 60mL). The combined ether extract was washed with water (100mL). The water wash was back-extracted with ether (3 × 60mL). The combined organic extracts were concentrated under vacuum, and the residues were subjected to column chromatography using 10% EtOAc/hexane to obtain 11-dodecyne -1-alcohol (7.4g,74%) contaminated with 3-5% of other regional isomers (regioisomer). TLC:30% EtOAc/hexane, Rf ≈ 0.4;1H NMR(300MHz,CDCl3)δ3.66(t,2H,J = 7.3Hz), 2.14-2.21(m,2H),1.93(t,J = 1.9Hz,1H),1.20-1.63(m,16H). |