Lithium Hydroxide → ({[2-(4-Methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acid

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Reaction Conditions

Reaction Steps

Ethyl ({[2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate (5.95 g, 16.8 mmol) was dissolved in THP (75 ml) and cooled to 0° C. LiOH (2.11 g, 50.4 mmol) in water (40 ml) was added and the mixture was stirred for 90 minutes. Water was added and the mixture was extracted twice with diethyl ether. The aqueous layer was acidified using 2M HCl until pH=4 and extracted twice with CH2Cl2. The combined CH2Cl2 layers were dried (Na2SO4) and concentrated under reduced pressure to afford 5.4 g (>98%) 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), 3.4 (s, 2H), 3.5 (s, 4H), 3.9 (s, 3H), 6.9 (d, 2H), 7.4 (d, 2H).

Provenance & Evidence