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

Temperature

82.5 °C

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.

1. customIn a 50 mL volume glass flask equipped with a stirrer
2. temperatureThe resulting mixture was refluxed
3. filtrationthe reaction mixture was filtered
4. concentrationconcentrated under reduced pressure
5. additionTo the concentrate was added n-heptane
6. customto precipitate a crystalline product
7. filtrationThe crystalline product was collected by filtration
8. customdried under reduced pressure

ORD record

ord-c1043cb2fef548468327b23dd924f06c

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367824B2