Diiodomethane → 12H-dibenzo[d,g][1,3]dioxocin-12-one

Temperature

105 °C

2,2'-Dihydroxybenzophenone (10.0 g, 46.7 mmol) and diiodomethane (13.1 g, 49 mmol) was dissolved in dry N,N-dimethylformamide (180 ml). Dried finely powdered potassium carbonate (9.2 g, 66.7 mmol) was added and the mixture was heated at 105° C. for 16 h. After cooling to room temperature the reaction mixture was poured into ice water (500 ml). The precipitate was collected by filtration after 0.5 h, washed with water on the filter and dissolved in a mixture of ethanol (80 ml) and 4 N sodium hydroxide (20 ml). The solution was stirred at reflux temperature for 1 h, cooled and diluted with water (300 ml). The formed crystalline precipitate was filtered off, washed with water (50 ml) and dried in vacuo, affording 12H-dibenzo[d,g][1,3]dioxocin-12-one as a solid (9.5 g, 90%).

1. additionwas added
2. temperatureAfter cooling to room temperature the reaction mixture
3. filtrationThe precipitate was collected by filtration after 0.5 h
4. washwashed with water on the
5. filtrationfilter
6. dissolutiondissolved in a mixture of ethanol (80 ml) and 4 N sodium hydroxide (20 ml)
7. temperatureat reflux temperature for 1 h
8. temperaturecooled
9. additiondiluted with water (300 ml)
10. filtrationThe formed crystalline precipitate was filtered off
11. washwashed with water (50 ml)
12. customdried in vacuo

ORD record

ord-7c53b691c4404fb19d65ab117d04d6d7

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06004961