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

Temperature

82.5 °C

In a 100 mL volume glass flask equipped with a stirrer, a thermometer and a reflux condenser were placed 10.2 g (54.9 mmol) of methyl 3-hydroxy-4-methoxybenzoate (purity: 98 wt. %), 11.5 g (71.4 mmol) of 3-bromo-1-chloropropane (purity: 98 wt. %), 8.5 g (60.4 mmol) of potassium carbonate (purity: 98 wt. %), and 30 mL of acetone. 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. To the concentrate was added n-heptane, to precipitate a crystalline product. The crystalline product was collected and dried under reduced pressure, to give 13.7 g (isolated yield: 95.8%, purity: 99% in terms of area percentage by high performance liquid chromatography) of methyl 3-(3-chloropropoxy)-4-methoxybenzoate as a white crystalline product.

1. customIn a 100 mL volume glass flask equipped with a stirrer
2. temperatureThe resulting mixture was refluxed
3. filtrationthe reaction mixture was filtered
4. additionTo the concentrate was added n-heptane
5. customto precipitate a crystalline product
6. customThe crystalline product was collected
7. customdried under reduced pressure

ORD record

ord-829a6f3db9e544b08ed0dbb0af98dab1

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367824B2