1,3-Dioxan-5-ol, 2,2-dimethyl- synthesis

6synthesis methods

Product Name:1,3-Dioxan-5-ol, 2,2-dimethyl-
CAS Number:3391-30-8
Molecular formula:C6H12O3
Molecular Weight:132.16

74181-34-3 Synthesis

74181-34-3
132 suppliers
$13.00/100mg

3391-30-8
26 suppliers
$250.00/500mg

Yield:3391-30-8 93.4%

Reaction Conditions:

Stage #1:2,2,-dimethyl-1,3-dioxan-5-one with lithium aluminium tetrahydride in diethyl ether at 0 - 8; for 1 h;
Stage #2: with sodium hydroxide in diethyl ether;water at 0 - 10;

Steps:

9.a
(9a) 2,2-dimethyl-1,3-dioxan-5-ol To a diethyl ether (150 ml) solution of 2,2-dimethyl-1,3-dioxan-5-one (15 g, 0.115 mol), lithium aluminum hydride (4.38 g, 0.115 mol) was added at 0 to 8° C. for one hour in a nitrogen atmosphere. To the reaction mixture, water (4.2 ml), a 5N aqueous sodium hydroxide solution (4.2 ml), and water (12.8 ml) were sequentially added dropwise at 0 to 10° C. The mixture was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound (14.2 g, 93.4%) as a colorless oil. ¹H NMR(400 MHz, CDCl₃) δppm; 1.44(3H, s), 1.46(3H, s), 2.75-2.95(1H, br), 3.51-3.55(1H, m), 3.74-3.79(2H, m), 4.05-4.10(2H, m).

References:

Eisai Co., Ltd. US2007/10542, 2007, A1 Location in patent:Page/Page column 33

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