Sodium hydride → 5-Ethyl-4-(2-methoxy-ethoxymethoxy)-2-methyl-benzaldehyde

Participants

Reaction Steps

A solution of 5-ethyl-4-hydroxy-2-methyl-benzaldehyde (0.9 g, 5.5 mmol) dissolved in THF (10 mL) was added to a cooled 0° C. suspension of NaH (0.29 g, 7.2 mmol, 60% dispersion in mineral oil) in THF (5 ml). After the addition was complete the reaction mixture was warmed up to room temperature and stirred for 30 mins. 2-Methoxyethoxymethyl chloride (0.82 mL, 7.1 mmol) was added and the reaction was stirred for 4 hours. The reaction mixture was quenched with 1N HCl and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a yellow oil. Purification by flash column chromatography (10% to 20% EtOAc in hexanes) gave the title compound as a clear oil (0.89 g, 65%). 1H NMR (400 MHz, CDCl3): δ 1.21 (t, J=7.3 Hz, 3H), 2.63 (m, 5H), 3.39 (s, 3H), 3.57 (m, 2H), 3.84 (m, 2H), 5.37 (s, 2H), 6.95 (s, 1H), 7.62 (s, 1H), 10.15 (s, 1H).

Provenance & Evidence