Hydrochloric Acid → 4-(1-Methoxycarbonyl-1-methyl-ethyl)-benzoic acid

Participants

Reaction Steps

5.60 g (27 mmol) of 2-(4-formyl-phenyl)-2-methyl-propionic acid methyl ester was dissolved in 112 mL of tert-butanol; 16.97 mL (11.20 g=136 mmol) of 2-methyl-2-butene was added, followed by a solution of 7.98 g (71 mmol) of sodium chlorite and 6.35 g (41 mmol) of sodium dihydrogen phosphate in 56 mL of water. After 20 hours, the reaction mixture was poured into crashed ice/EtOAc, the pH was adjusted to ˜3.0 with aq. HCl (1N) and it was extracted twice with EtOAc; the organic phases were washed with water, dried (MgSO4), filtered and evaporated. The crude product was purified by recrystallisation from EtOAc/heptane to give 3.00 g of the title compound as colorless solid. MS: 221.2 [(M−H)−].

Provenance & Evidence