Lithium Hydroxide → 2,2-Bis(4-nitrobenzyl)malonic acid

Participants

Reaction Steps

An adaptation of the procedure described by Tiefenbacher and Rebek (2012) was followed. To a suspension of 5.33 g (12.9 mmol) of 2,2-dimethyl-5,5-di(4-nitrobenzyl)-1,3-dioxane-4,6-dione in 60 mL of a 9:1 mixture of THF to water was added 1.11 g (46.3 mmol) LiOH. This suspension was stirred for ˜17 h. After stirring, 100 mL of water was added to the suspension. The aqueous solution was washed twice with 50 mL of diethyl ether. The aqueous solution was then acidified to pH=1. The product was extracted with ethyl acetate. The ethyl acetate solution was washed once with 100 ml of water and once with 100 mL of brine. The ethyl acetate solution was dried with MgSO4 and the solvent was removed in vacuo to yield 4.21 g (87%) of the desired material. IR, 1HNMR, 13CNMR in addition to TLC were used to confirm identity of the product.

Provenance & Evidence