Dehydrolinalool

Dehydrolinalool is a ynone.

To a solution of 6-methylhept-5-en-2-one (5.05 g, 40 mmol) in THF (100 mL) at -78 °C was added 0.5 M ethynylmagnesium bromide in THF (96 mL, 48.0 mmol) dropwsie through an addition funnel. The formed white slurry was allowed to warm up to rt and stirred for 2 h. Quenched with sat. NH796 mg of potassium hydroxide (KOH) in 45percent (wt. /vol.) aqueous solution and 20 194.5 g of 6-methyl-5-hepten-2-one (MH) were introduced into a reactor; the molar ratio KOH : MH was thus 1 : 250. After fourfold evacuation of the air from the reactor and subsequent flushing with nitrogen (inertisation of the reactor), 369 g of ammonia were introduced. Acetylene was then added to provide a pressure of 16.1 bar (1.61 MPa) at [30°C, ] corresponding to 21percent (wt. /vol.) of acetylene in the mixture of ammonia and 25 acetylene. The contents of the reactor were agitated by gas stirring. Samples were taken at various time intervals for analysis of their content by gas chromatography (GC). After 5 hours the reaction was finally stopped since by then it had been established that a predominant amount of the desired product, 3, [7-DIMETHYL-6-OCTEN-1-YN-3-OL] (dehydrolinalool; DLL) and only small amounts of diol by-product and unchanged MH were present. The results are presented in Table 1 below

Molecular Weight:152.23
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:152.120115130
Monoisotopic Mass:152.120115130
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:190
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes