Carbon Dioxide → HCID 14672052, compound

Participants

Reaction Steps

A mixture of Mg (10 mmol), 2-s-butyl-4-bromo-6-t-butyl-1-trimethylsiloxy benzene [which is prepared from 2-s-butyl-6-t-butylphenol by sequential reactions with bromine (CH2Cl2), 0° C., 15 min) and n-butyllithium (THF, -78° C., 15 min)/chlorotrimethylsilane (-78° C. to -25° C., 18 hr)] and a few drops of 1,2-dibromoethane in 25 ml THF is heated at reflux for two hr and then is added to an excess of pulverized dry ice. The resulting slurry is stirred for 1 hr, then added to a 300 ml portion of 1N NaOH and stirred for 1 hr. The resulting mixture is washed with 3×100 ml portions of ether, and then is made acidic with excess 3N HCl. The product is extracted with 3×200 ml portions of ethyl acetate. The combined organic portions are dried (MgSO4), filtered, and concentrated in vacuo to give 3 -s-butyl-4-hydroxy-5-t-butylbenzoic acid, used in the next step without further purification.

Provenance & Evidence