Hydrochloric Acid → HCID 20062264, compound

Participants

Reaction Steps

To a solution of 4.72 g (0.205 mol) of freshly cut sodium metal dissolved in absolute ethanol was added 16.8 g (0.105 mol) of diethyl malonate in 25 mL of absolute ethanol. To this solution was added 16.2 g (0.10 mol) of 1-(3-hydroxyphenyl)but-1-en-3-one, prepared as described by Marrion et al. in J. Biochem. vol. 45, 533, (1949), and 100 mL of absolute ethanol. The solution was stirred at ambient temperature for 17 hours, diluted with 500 mL of water and acidified with 19 mL of concentrated HCl. The mixture was diluted with 400 mL of methylene chloride and the organic layer separated, washed with 150 mL of water and dried over Na2SO4. The solvent was removed in vacuo leaving 26.5 g (96 percent of theoretical) of the above named product as a light yellow oil; 1H NMR (CDCl3 +D6 --DMSO) δ 0.8- 1.3 (m, 3H, --CH2CH3), 2.3-4.3 (m, 6H, ring protons and --CH2CH3), 5.5 (s, 1H, --CH=), 6.5-7.2 (m, 4H, ArH), 6.8 (b, 1H, ArOH), 18.0 (b, 1H, OH).

Provenance & Evidence