HCID 68524499, compound → HCID 59451682, compound

Participants

Reaction Steps

After careful purging with argon and still under an atmosphere of argon, 10% palladium on carbon (0.015 g, 0.015 mmol) was suspended in 8 mL ethanol. 7-(3-methoxyphenyl)hept-6-enoic acid (2) was dissolved in 2 mL warm ethanol and injected into the reaction solution and stirring was commenced. The reaction vessel was then purged with hydrogen gas after which a hydrogen balloon was utilized to maintain a hydrogen atmosphere in the reaction vessel while stirring continued for 18 hours. The 10% palladium on carbon was filtered off on diatomaceous earth and the ethanolic filtrate collected and condensed in vacuo to provide the desired product in 93% yield (0.159 g) as a light yellow oil without further purification: 1H NMR (500 MHz, CDCl3) δ 7.24 (q, 1H), 6.79 (q, 3H), 3.83 (s, 3H), 2.63 (t, 2H), 2.39 (t, 3H), 1.69 (m, 4H), 1.41 (m, 4H); 13C NMR (500 MHz, CDCl3) δ 180.48, 159.62, 144.33, 129.24, 120.90, 114.23, 110.93, 100.01, 55.11, 35.96, 34.13, 31.19, 28.94, 24.64.

Provenance & Evidence