Dimethylformamide → HCID 10825903, compound

Temperature

-20 °C

Oxalyl chloride (3.3 ml.) was added to a stirred solution of the 2-p-fluorophenyl-4-m-methoxyphenylbutyric acid thus obtained (6.7 g.) and dimethylformamide (0.05 ml.) in toluene (50 ml.) and the mixture was stirred at laboratory temperature for 2 hours and then evaporated to dryness. The residue was dissolved in methylene chloride (100 ml.), the solution was stirred and cooled to -20° C. and stannic chloride (3.2 ml.) was added. The mixture was stirred for 2 hours and then poured into ice-water (250 ml.) and the mixture was extracted three times with methylene chloride (100 ml. each time). The combined extracts were washed with saturated aqueous sodium bicarbonate solution and then with water, dried and evaporated to dryness and the residue was stirred with methanol. The mixture was filtered and there was thus obtained as solid residue 2-p-fluorophenyl-3,4-dihydro-6-methoxy -naphthalen-1(2H)-one, m.p. 124-127° C.

1. customevaporated to dryness
2. dissolutionThe residue was dissolved in methylene chloride (100 ml.)
3. stirringthe solution was stirred
4. additionstannic chloride (3.2 ml.) was added
5. stirringThe mixture was stirred for 2 hours
6. additionpoured into ice-water (250 ml.)
7. extractionthe mixture was extracted three times with methylene chloride (100 ml
8. washThe combined extracts were washed with saturated aqueous sodium bicarbonate solution
9. dry with materialwith water, dried
10. customevaporated to dryness
11. stirringthe residue was stirred with methanol
12. filtrationThe mixture was filtered

ORD record

ord-6bff0bb659b249ada06e0e77b7b76e4e

Source dataset

uspto-grants-1988_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04751240