Imidazole → HCID 23455017, compound

Participants

Reaction Steps

A flask is fitted with a stirring bar and charged with 5.0 grams (0.0255 mole) of 2-acetoxy-5-hydroxybenzoic acid [M. Bergmann and P. Dangschat, Berichte, 52, 371 (1919)]. After the flask is flushed with argon and cooled in an ice bath, a solution of t-butyldimethylsilylchloride (9.23 gr., 0.06122 mole) and imidazole (8.5 gr., 0.125 mole) dissolved in 20 ml of anhydrous dimethylformaldehyde (DMF) is added dropwise over a 30 minute period. The reaction mixture is stirred at room temperature overnight. The DMF is removed in vacuo. The residue is taken up in ether (75 ml) transferred to a separatory funnel and extracted with 1 N HCl (3×25 ml), 5% NaOH (3×25 ml), water (2×10 ml) and brine (20 ml). The ether extract is dried over sodium sulfate, filtered and the solvents removed in vacuo to yield 2-acetoxy-5-t-butyldimethylsilylbenzoic acid.

Provenance & Evidence