Water → 6-(beta-Chloroethoxy)-1-tetralone

To a solution of 6-hydroxy tetralone (2.0 g, 12.3 mmol) in DMF (50 mL) was added dry cesium carbonate (8.02 g, 24.6 mmol). Neat 2-chloroethyl-p-tolensulfonate (3.49 g, 14.9 mmol) was added to this mixture and the reaction stirred at room temperature for 58 hours. The reaction was poured into 200 mL of water and to this mixture was added 10 mL of 1N NaOH followed by 200 mL of Et2O. The mixture stirred at room temperature for 2 hours. The aqueous portion was separated and extracted with Et2O (3×200 mL). The combined organic portions were washed successively with 1N NaOH (2×100 mL), water (2×100 mL), and brine, dried, filtered, and concentrated under vacuum to give 5.07 g of a faintly orange solid. The solid was dissolved in minimal DCM and chromatographed (silica gel, 190 g, DCM). The appropriate fractions were pooled and concentrated under vacuum to afford 2.65 g (96%) of a white crystalline solid:

1. additionNeat 2-chloroethyl-p-tolensulfonate (3.49 g, 14.9 mmol) was added to this mixture
2. stirringThe mixture stirred at room temperature for 2 hours
3. customThe aqueous portion was separated
4. extractionextracted with Et2O (3×200 mL)
5. washThe combined organic portions were washed successively with 1N NaOH (2×100 mL), water (2×100 mL), and brine
6. customdried
7. filtrationfiltered
8. concentrationconcentrated under vacuum
9. customto give 5.07 g of a faintly orange solid
10. customchromatographed (silica gel, 190 g, DCM)
11. concentrationconcentrated under vacuum

ORD record

ord-89b09b61df49493b97351337f3d54eb3

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265422B1