2-Chloroethyl methyl ether → HCID 58442521, compound

Participants

Reaction Conditions

Reaction Steps

A pressure glass vessel charged with 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (500 mg, 3.1 mmol, 1.0 equiv) and 1-chloro-2-methoxyethane (0.28 mL, 3.1 mmol, 1.0 equiv) in 50% aqueous NaOH solution (5.0 mL) was heated at 140° C. for 16 h. The residue was diluted with H2O (20 mL) and extracted with EtOAc (3×30 mL). The organic layer was separated, dried with MgSO4, and concentrated under reduced pressure to give 1-(4-(2-methoxyethoxy)-2,6-dimethylphenyl)ethanone (430.9 mg, 1.9 mmol) as yellow oil in 64% yield: 1H NMR (CDCl3, 500 MHz) δ 6.58 (s, 2 H), 4.09-4.10 (m, 2 H), 3.72-3.74 (m, 2 H), 3.44 (s, 3 H), 2.45 (s, 3 H), 2.23 (s, 6 H); ESI-MS: m/z 223.6 (M+H)+.

Provenance & Evidence