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ChemicalBook CAS DataBase List 9-Hydroxycapric acid
1422-27-1

9-Hydroxycapric acid synthesis

10synthesis methods
-

Yield: 86%

Reaction Conditions:

with lithium hydroxide in tetrahydrofuran;methanol at 0 - 20; for 3 h;

Steps:

6.c EXAMPLE 5 9-oxodecanoic Acid
c) 9-hydroxydecanoic Acid (0065) Methyl 9-hydroxydecanoate (0.3108 g, 1.536 mmol) was dissolved in THF (5 ml) and methanol (5 ml) and cooled to 0° C. Next, lithium hydroxide (0.922 ml, 1.844 mmol) was added and the reaction was warmed to room temperature. The progress was monitored by TLC (70:30 hexane:EtOAc) staining with KMnO4. After 3 hours, starting material still remained so an additional 0.9 ml of 2M LiOH was added and stirring was continued. After 6 hours, a TLC showed that the starting material had largely been consumed. The reaction was concentrated on the rotavap to remove the methanol and THF. The residue was diluted with 1M KOH (15 ml) and washed with MTBE (2×30 ml). The aqueous layer was cooled to 0° C. and adjusted to pH1 by dropwise addition of concentrated HCl. The product was extracted using ethyl acetate (2×50 ml). The ethyl acetate layer was dried (Na2SO4), filtered and concentrated providing a clear oil. The oil was placed on the vacuum pump overnight at 50° C. providing the 9-hydroxydecanoic acid (0.25 g, 86%) as a clear oil. 1H NMR (300 MHz, CDCl3, ppm) 1.19 (d, J=6H, 3H), 1.25-1.45 (m, 11H), 1.5-1.66 (m, 2H), 2.35 (t, J=7 Hz, 2H), 3.76-3.83 (m, 1H); 13C NMR (75 MHz, CDCl3, ppm) 23.7, 24.8, 25.8, 29.1, 29.3, 29.6, 34.1, 39.5, 68.4, 179.1.

References:

Givaudan S.A.;Jordan, Jason;Bom, David C.;Christenson, Philip A.;Eilerman, Robert G.;Yang, Xiaogen US9480280, 2016, B2 Location in patent:Page/Page column 9-10