Water → 2-Hydroxy-2-methylcyclohexan-1-one

In a 50 ml flask equipped with a thermometer, a dropping funnel, and a stirrer were charged 7 ml of methylene chloride, 7 ml of water, 2 mmole of 1-methyl-1-cyclohexene, and 0.1 mmole of each of ruthenium catalysts shown in Table 2 below. To the mixture was added dropwise a 30% ethyl acetate solution of 1.52 g (6 mmole) of peracetic acid at room temperature over 2 hours while stirring on a magnetic stirrer. After the addition, the stirring was further continued at room temperature for 2 hours. The reaction mixture was extracted three times with 20 ml portions of methylene chloride. The extract was washed with 30 ml of a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the residual crude product was purified by silica gel column chromatography using a 5:1 (by volume) mixture of n-hexane and ethyl acetate as an eluent to obtain 2-methyl-2-hydroxy-1-cyclohexanone. The percent yield of the product is shown in Table 2.

1. customIn a 50 ml flask equipped with a thermometer, a dropping funnel, and a stirrer
2. additionAfter the addition
3. extractionThe reaction mixture was extracted three times with 20 ml portions of methylene chloride
4. washThe extract was washed with 30 ml of a saturated sodium chloride aqueous solution
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was removed by distillation
7. customthe residual crude product was purified by silica gel column chromatography
8. additiona 5:1 (by volume) mixture of n-hexane and ethyl acetate as an eluent

ORD record

ord-776dcd429e524bf6ba2341d516752278

Source dataset

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05210315