Dimethyl 2,2'-(1,3-dioxolane-2,2-diyl)diacetate → 1,3-Dioxolane-2,2-diethanol

To a solution of 2.6 g (12 mmol) of dimethyl 2,2′-(1,3-dioxolane-2,2-diyl)diacetate in 100 mL of dry THF was added 1.4 g (36 mmol) of LAH at 0° C. The reaction mixture was then refluxed for 1 h, was quenched with 15% NaOH aqueous solution (3 mL) and water (3 mL). The mixture was stirred overnight, filtered through celite. The residue was washed twice with THF (100 mL×2). The combined organic phase was evaporated. Chromatography on silica gel afforded 1.3 g (8.0 mmol, yield: 66%) of 2,2′-(1,3-dioxolane-2,2-diyl)diethanol: MS (m/e): 163 (M+1)+.

1. temperatureThe reaction mixture was then refluxed for 1 h
2. customwas quenched with 15% NaOH aqueous solution (3 mL) and water (3 mL)
3. filtrationfiltered through celite
4. washThe residue was washed twice with THF (100 mL×2)
5. customThe combined organic phase was evaporated

ORD record

ord-14f06a0977364f31a6b4e2d539cc14a3

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362003B2