Isobutylene → HCID 21187905, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of isobutylene (33 mL) in dichloromethane (60 mL) at −70° C. is treated dropwise with a cooled solution of methyl 3-hydroxy-4-methoxybenzoate (6 g) in dichloromethane (60 mL), followed by trifluoromethanesulfonic acid (0.3 mL). The reaction mixture is vigorously stirred at −70° C. for 3 hours and then between −70° C. and −50° C. overnight. It is then treated with triethylamine (0.6 mL) and allowed to warm to room temperature. The resulting yellow solution is concentrated, and the residue is subjected by mplc, using diethyl ether as eluent, to give methyl 3-tert-butoxy-4-methoxybenzoate (4.93 g), m.p. 98-100° C. [Elemental analysis: C,65.7; H,7.8%; calculated: C,65.5; H,7.6%].

Provenance & Evidence