2-Isopropyl-5-methyl-cyclohexanecarboxylic acid (2-hydroxy-2-phenylethyl)-amide → 2-Isopropyl-5-methyl-cyclohexanecarboxylic acid (2-oxo-2-phenyl-ethyl)-amide

A 20 mL round bottom flask equipped with a stir bar was charge with 2-Isopropyl-5-methyl-cyclohexanecarboxylic acid (2-hydroxy-2-phenyl-ethyl)-amide (100 mg, 0.33 mmol) and acetic acid (1 mL). A solution of CrO3 (36 mg, 0.363 mmoles, 1.1 eq) in acetic acid (500 μl) and water (100 μl) was slowly added to the reaction mixture. The reaction mixture was stirred at ambient temperature for 15 min and diluted with ethyl acetate (30 mL) and saturated NaHCO3 (aq.) (30 mL). The heterogeneous mixture was transferred to a reparatory funnel where the aqueous phase was separated and re-extracted with ethyl acetate (2×10 mL). The organic phases were combined and washed with sat NaHCO3 (3×10 mL), H2O (10 mL), brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (30% to 50% ethyl acetate/hexane for elution) provided the title compounds as white solid (92 mg, 93%).

1. customA 20 mL round bottom flask equipped with a stir bar
2. customThe heterogeneous mixture was transferred to a reparatory funnel
3. customwhere the aqueous phase was separated
4. extractionre-extracted with ethyl acetate (2×10 mL)
5. washwashed with sat NaHCO3 (3×10 mL), H2O (10 mL), brine (10 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by flash chromatography on silica gel (30% to 50% ethyl acetate/hexane for elution)

ORD record

ord-0437bf243909409ca33fa01cce5405c3

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618155B2