Hydrochloric Acid → HCID 14291555, compound

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.

1. customto rise to room temperature
2. stirringstirred for 16 h
3. customThe organic phase was then separated
4. extractionthe aqueous phase was extracted three times with 20 mL aliquots of dichloromethane
5. extractionThe combined dichloromethane extract
6. washwas washed successively with 20 mL of 0.1 N NaOH and 20 mL
7. distillationdistilled water
8. extractionThe dichloromethane extract
9. dry with materialwas then dried (Na2SO4)
10. filtrationfiltered
11. customevaporated
12. customto give a cream
13. customThe crude product was crystallized from ethanol

ORD record

ord-75ad71c6a83d493bb1c49687b4158b26

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06121275