3,5-Dimethylbenzoic acid → 3,5-Dimethylbenzoyl Chloride

3,5-Dimethylbenzoic acid (25 g, 0.17 mol) and dimethylformamide (0.1 mL) were added to thionyl chloride (50 mL) at 0° C. The mixture was refluxed under beating for 2 h. The excess thionyl chloride was evaporated under reduced pressure and to the residue was added toluene (50 mL). Toluene was evaporated under reduced pressure to give oily 3,5-dimethylbenzoyl chloride. A solution of propyleneimine (14 mL, 0.18 mol) in tetrahydrofuran (160 mL) was added to 1N aqueous sodium hydroxide solution (180 mL). 3,5-Dimethylbenzoyl chloride was added dropwise to this mixture at 0° C. After completion of dropwise addition, the mixture was stirred further for 30 min. The reaction mixture was extracted with ethyl acetate. The extract was dried, and the solvent was evaporated to give the title compound (31 g, 0.16 mol, yield 99%). oil.

1. temperatureThe mixture was refluxed
2. customThe excess thionyl chloride was evaporated under reduced pressure and to the residue
3. additionwas added toluene (50 mL)
4. customToluene was evaporated under reduced pressure

ORD record

ord-b9f95bbef320444c8401943cb0cc23eb

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06962933B1