3-Methyl-2-buten-1-OL → 2-[(3-Methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione

Participants

Reaction Steps

To a stirred solution of 2-hydroxynaphthalene-1,4-dione (10.0 g, 57.4 mmol) and triphenylphosphine (15.1 g, 57.4 mmol) in dry tetrahydrofuran (150 ml) at 0° C. under an atmosphere of nitrogen was added diethyl azodicarboxylate (10.0 g, 57.4 mmol). After stirring for a further 5 minutes, a solution of 3-methylbut-2-enol (7.42 g, 86.1 mmol) in dry tetrahydrofuran (10 ml) was added dropwise and stirring was continued for 2 hours. The precipitate was collected, air-dried and recrystallised from aqueous methanol to yield the title compound (8.3 g) as a yellow crystalline solid with a melting point of 138° C.

Provenance & Evidence