Dimethylformamide → Benzyl cyclohexanecarboxylate

To a solution of cyclohexanecarboxylic acid (2.56 g) in dichloromethane (50 ml) and N,N-dimethylformamide (0.5 mL) was added oxalyl chloride (1.92 mL) under ice cooling. The solution was stirred at room temperature for 1 hour and then concentrated under reduced pressure. A solution of the resulting residue in dichloromethane (30 mL) was added to a solution of benzyl alcohol (2.4 g) and triethylamine (8.4 mL) in dichloromethane (30 mL) under ice cooling. The solution was stirred under ice cooling for 1 hour, and then it was washed in turn with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The solution was dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=9:1) to give the title compound (3.44 g).

1. concentrationconcentrated under reduced pressure
2. additionA solution of the resulting residue in dichloromethane (30 mL) was added to a solution of benzyl alcohol (2.4 g) and triethylamine (8.4 mL) in dichloromethane (30 mL) under ice cooling
3. stirringThe solution was stirred under ice cooling for 1 hour
4. washit was washed in turn with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
5. dry with materialThe solution was dried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=9:1)

ORD record

ord-09faa19d1b5f455e81751b4c04eedde9

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07375115B2