4-Methoxymethylene-1,1-dimethyl-cyclohexane → 4,4-Dimethylcyclohexane-1-carbaldehyde

Temperature

0 °C

A solution of flask 4-(methoxymethylene)-1,1-dimethylcyclohexane (2.3 g, 14.9 mmol) in a 4:1 THF/2N HCl mixture (100 mL) was refluxed fo(1 hour. The volatile was removed in vacuo and the residue was cooled to 0°C. and neutralized with 1N NaOH and extracted with Et2O (3×60 mL). The organic layer was washed with water (50 mL), brine (60 mL) and dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography with hexane-DCM 10% linear gradient as eluant to give the title compound as clear oil. 1H NMR (400 MHz, CDCl3) δ 9.64 (d, J=1.6 Hz, 1H), 2.19-2.12 (m, 1H), 1.79-1.72 (m, 2H), 1.59-1.40 (m, 5H), 1.25-1.18 (m, 1H), 0.92 (s, 3H), 0.87 (s, 3H). No ionization by LCMS.

1. custom1 hour
2. customThe volatile was removed in vacuo
3. extractionextracted with Et2O (3×60 mL)
4. washThe organic layer was washed with water (50 mL), brine (60 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by chromatography with hexane-DCM 10% linear gradient as eluant

ORD record

ord-105ee5a9710f45f5a6038f5754e1cf3f

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150568B2