2-Methyl-2-butene → HCID 71185803, compound

Participants

Reaction Steps

To a mixture of 8-chloro-4-methoxy-1-naphthaldehyde (step-3 intermediate) (2.0 g, 9.06 mmol) in tBuOH (20 mL) and 2-methyl-2-butene (14.4 mL, 136.0 mmol) at 0° C. was added a solution of NaClO2 (4.1 g, 45.3 mmol) and NaH2PO4.H2O (6.3 g, 45.3 mmol) in H2O (16 mL) dropwise. The resulting solution was stirred at RT for 24 h. The solvent was evaporated and the crude mixture was basified with 10% NaOH solution and then washed with EtOAc. The aqueous layer was acidified with 1 N HCl and again extracted with EtOAc. The combined organic layer was washed with water, brine, dried (Na2SO4) and filtered. The solvent was evaporated to provide the desired acid as pale yellow solid (1.7 g, 80%).

Provenance & Evidence