Water → 4-(2-Hydroxyethyl)cyclohexan-1-one

To a solution of 10 g (69 mmol) of 4-(2-hydroxyethyl)cyclohexanol in 50 mL of acetic acid maintained at a temperature between 18 and 21° C. are added over 35 min 35.9 mL (79 mmol) of an aqueous sodium hypochlorite solution. The mixture is further stirred for 45 min, TLC analysis indicating disappearance of starting material. Isopropanol (0.8 mL) is added, followed 10 min later by water (75 mL) and dichloromethane (100 mL). The two phases are separated by decantation and the aqueous phase is extracted with dichloromethane (50 mL). Combined organic phases are washed with an aqueous 3N sodium hydroxide solution (70 mL). This alcaline aqueous phase is extraced back with dichloromethane (30 mL). Combined organic phases are dried over magnesium sulfate and concentrated under reduced pressure to give 9.42 g (95%) of the title compound.

1. customThe two phases are separated by decantation
2. extractionthe aqueous phase is extracted with dichloromethane (50 mL)
3. washCombined organic phases are washed with an aqueous 3N sodium hydroxide solution (70 mL)
4. dry with materialCombined organic phases are dried over magnesium sulfate
5. concentrationconcentrated under reduced pressure

ORD record

ord-c91e98a6ff7349f5b79d5208641ee803

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802678B2