Hydrochloric Acid → HCID 14291555, compound

Participants

Reaction Steps

A solution of 3,4-dimethoxyphenylacetyl chloride (3.25 g, 15 mmol) in 15 mL freshly distilled dry dichloromethane was added dropwise to a stirred mixture of 1,3-benzodioxole (1.83 g, 15 mmol) and tin(IV) chloride (4.6 g, 17.6 mmol) in 15 mL dichloromethane at -10° C. The mixture was then allowed to rise to room temperature and was stirred for an additional 2 h. The reaction mixture was then poured into 25 mL 6 N HCl and stirred for 16 h. The organic phase was then separated and the aqueous phase was extracted three times with 20 mL aliquots of dichloromethane. The combined dichloromethane extract was washed successively with 20 mL of 0.1 N NaOH and 20 mL distilled water. The dichloromethane extract was then dried (Na2SO4), filtered, and evaporated to give a cream colored solid. The crude product was crystallized from ethanol to give 3.0 g of white needles of 11b in 66% yield; mp 110-111° C.; IR (Nujol) 2725, 1675, 1589,1519; 1H NMR δ 3.80 (s, 3H), 3.81 (s, 3H), 4.09 (s, 2H), 5.96 (s, 2H), 6.76 (m, 4H), 7.42 (d, I H, J=1.5), 7.58 (dd, 1H, J=6.4, 1.5); 13C NMR δ 45.3, 56.3, 102.3, 108.3, 108.7, 111.8, 112.7, 112.9, 121.9, 125.4, 127.7, 131.8, 148.4, 148.6, 149.4, 152.2, 196.4; Anal. calcd for C17H16O5 : C, 67.99, H, 5.37; Found: C, 67.98. H, 5.32.

Provenance & Evidence