Potassium Carbonate → (2,2-Diethoxyethyl)(3-methoxyphenyl)sulfane

Participants

Reaction Steps

Bromoacetaldehyde diethyl acetal (16.5 ml, 0.11 mol) was added dropwise to a mixture of m-methoxybenzenethiol (15.0 ml, 0.12 mol) and K2CO3 (16.6 g, 0.12 mol) in acetone (150 ml) at room temperature. The reaction mixture was stirred for 16 hours and then filtered. The solid was washed with acetone, and the combined filtrate and washes were concentrated in vacuo. The residue was diluted with H2O and extracted with Et2O. The Et2O extracts were washed with 0.5M KOH, H2O, and brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 27.4 g of 1-[(2,2-diethoxy)ethylthio]-3-methoxybenzene as a dark yellow oil. 'H NMR, δ: (CDCl3): 1.18 (6H, t, --OCH2CH3); 3.13 (2H, d, --SCH--); 3.43--3.73 (4H, m, --OCH2CH3); 3.77 (3H, s, -- OCH3); 4.67 (1H, t, --SCH2CH--); 6.60-7.27 (4H, m, aromatics).

Provenance & Evidence