Hydrogen Peroxide → (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide

A solution of 0.105 g (0.634 mmol) of (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarbonitrile in 4.9 mL of dimethyl sulfoxide was placed in a 10 mL flask with a magnetic stir bar. After adding 0.60 mL of 35% hydrogen peroxide and 0.097 g (1.2 mmol) of 50% sodium hydroxide solutions the flask was capped and stirred at room temperature for 20 h. The reaction mixture was diluted with 10 mL of water, extracted twice with 10 mL of methylene chloride. The combined methylene chloride layers were back extracted with 3×20 mL of water, dried over magnesium sulfate, and concentrated in vacuo to provide an off-white solid that was further purified by column chromatography (silica gel, 75:25 hexane:ethyl acetate) to provide (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide.

1. customwas capped
2. extractionextracted twice with 10 mL of methylene chloride
3. extractionThe combined methylene chloride layers were back extracted with 3×20 mL of water
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated in vacuo
6. customto provide an off-white solid
7. customthat was further purified by column chromatography (silica gel, 75:25 hexane:ethyl acetate)

ORD record

ord-a97f5bb11f954bae87492f963bccf1c9

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08754259B2