Lithium Hydroxide → {[(5,5-Dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetic acid

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Reaction Conditions

Reaction Steps

Ethyl {[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetate (11.2 g, 34.3 mmol) was dissolved in THF (150 ml) and cooled to 0° C. LiOH (2.88 g, 68.7 mmol) in water (40 ml) was added and the mixture was stirred for 19 h. The solvents were evaporated. The crude-product was extracted between water and diethyl ether. The aqueous layer was acidified to a pH of 6 using 2M HCl and extracted twice with CH2Cl2. The combined CH2Cl2 layers were dried (Na2SO4) and concentrated under reduced pressure to give 9.8 g (96%) of the title compound as a white solid. 1H-NMR (CDCl3, 200 MHz): δ 0.6 (s, 3H), 1.4 (s, 3H), 3.0 (s, 2H), 3.3 (s, 2H), 3.5 (s, 4H), 7.3-7.6 (m, 5H).

Provenance & Evidence