Sodium Chloride → (2,2-Dimethyl-1,3-dioxan-5-yl)methanol

HRID 546164Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[O:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:12][C:9]1([CH3:13])[O:10][CH2:11][CH:6]([CH2:4][OH:3])[CH2:7][O:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2,2-dimethyl-[1,3]dioxane-5-carboxylic acid ethyl ester (7.03 g, 37.35 mmol) in tetrahydrofuran (20 ml) was added dropwise to a cooled to 0° C. suspension of lithium aluminum hydride (1.8 g, 48.55 mmol) in tetrahydrofuran (20 ml). The reaction was stirred at 0° C. for 20 min and at 25° C. for 2 h. After such time, ethyl acetate (1 ml) and a few crystals of sodium sulphate decahydrate were added with caution. After stirring at 25° C. for 1 h saturated sodium chloride solution was added and the product extracted with ethyl acetate (3×100 ml). The organics were washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo to afford (2,2-dimethyl-[1,3]dioxan-5-yl)-methanol (4.09 g, 76%) as a clear oil: 1H NMR (300 MHz, CDCl3) δ ppm 1.39 (s, 3H, CH3), 1.44 (s, 3H, CH3), 1.79-1.90 (m, 1H, CH), 2.15-2.26 (brs, 1H, OH), 3.69-3.81 (m, 2H, 2×OCH of 2×OCH2), 3.74 (d, J=6.8 Hz, 2H, OCH2), 3.96-4.05 (m, 2H, 2×OCH of 2×OCH2).

Workup

additionwas added
extractionthe product extracted with ethyl acetate (3×100 ml)
washThe organics were washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0104e92189c44ffda073cd3fe41aefc7
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935699B2

Reaction notes

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