Hydrochloric Acid → HCID 19907982, compound

Participants

Reaction Conditions

Reaction Steps

All three compounds were prepared by the etherification of the corresponding alcohols with allyl bromide. An example is presented below. Sodium hydride (3.06 g, 0.128 mol) was suspended in dried THF (150 mL). The solution was bubbled with nitrogen and cooled to 0° C. 4-[2-(2-Hydroxyethoxy)ethoxy]benzaldehyde (26.8 g, 0.128 mol) was added dropwise to the solution. After the addition was completed, the resulting solution was stirred for 0.5 hr. Allyl bromide (23.2 g, 0.191 mol) was added. The reaction mixture was stirred at room temperature for 3 hr, acidified with 5% HCl aqueous solution (100 ml) and extracted with ethyl acetate. The collected organic phase was washed with 2% sodium bicarbonate aqueous solution, water, saturated sodium chloride solution, and dried over anhydrous MgSO4. The solvent was evaporated in a rotavapor and the residual oil was vacuum distilled at 136° C./7 mmHg to yield 20 g (63%) of a colorless oily product 6. 1 H-NMR (CDCl3, TMS, δ in ppm): 3.56-4.27 (m, 10H, --CH2 --(O--CH2 --CH2)--2), 5.23 and 5.78 (m, 3H, CH2 =CH--), 7.05 and 7.77 (2d, 4 aromatic protons), 9.86 (s, 1H, --CHO).

Provenance & Evidence