Lithium Hydroxide → HCID 19900662, compound

Participants

Reaction Steps

3,5-Bis(1,1-dimethylethyl)-4-hydroxy-α-oxo-benzeneacetic acid, methyl ester (20.0 g, 68.4 mmol) and LiOH (3.2 g, 439.1 mmol) are combined in 125 mL of a water-methanol-tetrahydrofuran mixture (1:1:1). The reaction warms to ca 50° C. and is maintained at this temperature using a heating bath for 5 hours under nitrogen atmosphere. The reaction is poured onto ice water and extracted with diethyl ether (3×). The cold aqueous layer is acidified with aqueous 12N HCl and extracted with diethyl ether (3×). The combined ethereal layers from the second extraction are washed with saturated aqueous NaCl, dried over Na2SO4, and concentrated in vacuo to give an oil. Crystallizing from diethyl ether/pentane gives 14.0 g of a first crop (mp 125°-126° C.) and 2.7 g as a second crop (mp 124°-125.5° C.). The total yield is 16.7 g (19.0 g theor., 88%).

Provenance & Evidence