2-Tert-Butylphenol → 7-(1,1-Dimethylethyl)-2,3-benzofurandione

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Reaction Steps

A mixture of 2-tert-butylphenol (15 g, 0.1 mmol) and 4-dimethylaminopyridine (0.5 g) is stirred under nitrogen in 300 ml of dichloromethane. Oxalyl chloride (20 ml, 0.22 moles) is added dropwise, then the mixture is heated to reflux. After ten hours the mixture is cooled and the solvent is removed under reduced pressure. The residue is taken up in 100 ml of 1,2-dichloroethane and added dropwise under nitrogen to a suspension of aluminum chloride (40 g, 0.3 mmol) in 300 ml of 1,2-chloroethane. After 20 hours at room temperature the mixture is slowly diluted with water until all solids dissolve. The organic layer is separated and dried over molecular sieves, and the solvent is evaporated to leave a syrup which is taken up in chloroform and filtered through a short column of silica gel. The filtrate is stripped of solvent under reduced pressure to leave the product (9.8 g) as a syrup suitably pure for subsequent reactions.

Provenance & Evidence