Potassium Carbonate → 1-(4-(Cyclopropylmethoxy)-2,6-dimethylphenyl)ethanone

HRID 1465521Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1.Cl[CH2:14][CH:15]1[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:15]1([CH2:14][O:1][C:2]2[CH:3]=[C:4]([CH3:12])[C:5]([C:9](=[O:11])[CH3:10])=[C:6]([CH3:8])[CH:7]=2)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

A vigorously stirred mixture of 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (4-2, 1.00 g, 10.9 mmol), chloromethylcyclopropane (4-1, 1.22 g, 7.4 mmol), and powdered potassium carbonate (1.54 g, 11.1 mmol) in DMF (10.0 mL) was heated at 80° C. for 16 h under N2. The mixture was allowed to cool and was filtered through Diatomaceous earth. The filtrate was concentrated under reduced pressure and the residue was extracted with EtOAc. The organic layer was washed with saturated aqueous sodium carbonate and dried over Na2SO4. The solution was concentrated under reduced pressure to provide 1-(4-(cyclopropylmethoxy)-2,6-dimethylphenyl)ethanone (4-3, 1.61 g) as off-white solids in 99% yield: 1H NMR (500 MHz, CDCl3) δ 6.55 (s, 2 H), 3.77 (d, J=6.9 Hz, 2 H), 2.45 (s, 3 H), 2.27 (s, 6 H), 1.19 (s, 1 H), 0.64 (m, 2 H), 0.33 (m, 2 H).

Workup

temperatureto cool
filtrationwas filtered through Diatomaceous earth
concentrationThe filtrate was concentrated under reduced pressure
extractionthe residue was extracted with EtOAc
washThe organic layer was washed with saturated aqueous sodium carbonate
dry with materialdried over Na2SO4
concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-3158ef2885384059bf496b616b3501ff
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999983B2

Reaction notes

Loading…