4-Toluenesulfonyl chloride → 1400591-99-2

0.63 g of p-toluenesulfonyl chloride was added to a solution of 0.522 g of ethyl 4-hydroxycyclohexanecarboxylate in 5.0 ml of pyridine. The reaction was stirred at room temperature for 3 hours. The reaction mixture was concentrated in vacuo. The resulting solid was taken up in water and ethyl acetate, and the organic phase was washed three times with 2N hydrochloric acid and once with saturated NaCl solution. The organic phase was dried over sodium sulfate and concentrated in vacuo. The resulting product was employed without further purification in the next step. The resulting product (0.55 g) was dissolved in 11.2 ml of DMF, and 0.159 g of phenol and 0.549 g of cesium carbonate were added. The solution was then heated at 80° C. for 6 hours. After cooling, the mixture was concentrated in vacuo and purified by column chromatography on silica gel (eluent: ethyl acetate/n-heptane 1:1). The desired product was obtained. Molecular weight 248.32 (C15H20O3), MS: 249 (M+H+).

1. concentrationThe reaction mixture was concentrated in vacuo
2. washethyl acetate, and the organic phase was washed three times with 2N hydrochloric acid
3. dry with materialThe organic phase was dried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe resulting product was employed without further purification in the next step
6. dissolutionThe resulting product (0.55 g) was dissolved in 11.2 ml of DMF
7. addition0.159 g of phenol and 0.549 g of cesium carbonate were added
8. temperatureThe solution was then heated at 80° C. for 6 hours
9. temperatureAfter cooling
10. concentrationthe mixture was concentrated in vacuo
11. custompurified by column chromatography on silica gel (eluent: ethyl acetate/n-heptane 1:1)

ORD record

ord-bf78828a9ac24c358148e3783502e097

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07223788B2