Boron trifluoride etherate → 2-(o-Tolyl)cyclohexanol

Temperature

-78 °C

To a solution of 1-bromo-3-methyl-benzene in THF at −78° C., was added dropwise a solution of nBuLi (1.6M in THF, 12.4 ml) and the reaction mixture was stirred at −78° C. for 30 minutes. After such time, 7-oxa-bicyclo[4.1.0]heptane (3.4 g) was added slowly to the reaction mixture followed by the addition of boron trifluoride etherate (2.5 ml). The reaction mixture was stirred at −78° C. for another 2 hours before allowing it to warm up to room temperature. The solution was then treated with solution of ammonium chloride (25 ml), the phases were separated and then extracted twice with ethyl acetate. The combined organic extracts were then washed with water, dried over sodium sulfate and concentrated in vacuo. The residue was then purified by column chromatography to give 2.9 g of (cis/trans) 2-o-tolyl-cyclohexanol MS(EI) 190.1 (M+).

1. stirringThe reaction mixture was stirred at −78° C. for another 2 hours
2. temperatureto warm up to room temperature
3. customthe phases were separated
4. extractionextracted twice with ethyl acetate
5. washThe combined organic extracts were then washed with water
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customThe residue was then purified by column chromatography

ORD record

ord-69dee6e1595449b08b1b5be0a4472616

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07411093B2