1-Bromo-3-chloropropane → Methyl 4-(3-chloropropoxy)-3-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

In a 50 mL volume glass flask equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser were placed 1.02 g (5.49 mmol) of methyl 4-hydroxy-3-methoxybenzoate (purity: 98 wt. %), 1.15 g (7.14 mmol) of 3-bromo-1-chloropropane (purity: 98 wt. %), 0.85 g (6.04 mmol) of potassium carbonate (purity: 98 wt. %), and 30 mL of acetonitrile. The resulting mixture was refluxed under stirring at 80-85° C. for 8 hours in an argon gas atmosphere. After the reaction was complete, the reaction mixture was filtered and concentrated under reduced pressure. To the concentrate was added n-heptane, to precipitate a crystalline product. The crystalline product was collected by filtration and dried under reduced pressure, to obtain 1.34 g (isolated yield: 97.8%, purity: 98% in terms of area percentage determined by high performance liquid chromatography) of methyl 4-(3-chloropropoxy)-3-methoxybenzoate as a white crystalline product.

Provenance & Evidence