ChemicalBook CAS DataBase List 11-HEXADECYN-1-OL

11-HEXADECYN-1-OL synthesis

15synthesis methods

Product Name:11-HEXADECYN-1-OL
CAS Number:65686-49-9
Molecular formula:C16H30O
Molecular Weight:238.41

56683-54-6 Synthesis

56683-54-6
86 suppliers
inquiry

107-21-1 Synthesis

107-21-1
1327 suppliers
$10.00/25g

65686-49-9
29 suppliers
inquiry

Yield: 80%

Reaction Conditions:

with sodium hydroxide;bromine

Steps:

3 Preparation of 11-Hexadecyn-1-ol from cis-11-Hexadecen-1-ol
EXAMPLE 3 Preparation of 11-Hexadecyn-1-ol from cis-11-Hexadecen-1-ol Cis-11-Hexadecen-1-ol (4.94 g, 20.4 mmoles, Sigma) was placed in a 25 ml 3-neck roundbottom flask equipped with a thermometer, an overhead mechanical stirrer, and a reflux condenser. The contents of the flask were cooled to 15° C. and bromine (3.28 g, 20.4 mmole) was added slowly with stirring at such a rate as to keep the reaction temperature below 30° C. After addition of the bromine, the reaction was stirred at room temperature for 10 minutes. Polyethylene glycol 300 (0.5 g, Fluka) was added followed by powdered sodium hydroxide (2.05 g, 51.25 mmoles). A large exotherm was noted which brought the reaction temperature to 150° C. The reaction was stirred vigorously with heating to maintain a temperature of 125° C. for 2.5 hours. The reaction was cooled and filtered to remove the solid sodium bromide. The filtered salts were washed with 25 ml of hexanes and the solvent removed in vacuo. The crude product was kugelrohr distilled (ca. 160° C./ 0.20 torr) to yield 11-hexadecyn-1-ol (3.88 g, 80% yield) as a clear colorless liquid. ¹ H NMR (CDCl₃): 3.67 (m) 2.45 (m), 1.03-1.68 (m) ¹³ C NMR(CDCl₃): 79.91, 79.88, 62.38, 32.50, 31.06, 29.40, 29.28, 28.96, 28.64, 25.61, 21.70, 18. 52, 18.21, 13.38. IR (thin film): 3300, 2910, 2820, 1460, 1150

References:

Kenkel Research Corporation US5093536, 1992, A