Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dimethyl acetylenedicarboxylate | HCID 12980 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Benzyltrimethylammonium hydroxide | HCID 66854 | — |
| Reactant | HCID 21504768 | HCID 21504768 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 21504764 | HCID 21504764 | — |
Reaction Steps
The starting compound was obtained in the following way: A solution of 9.8 gm (0.04 mol) of 2-chloro-3-hydroxy6H-dibenzo-[b,d]-pyran and 9.0 gm (0.06 mol) of dimethyl acetylene-dicarboxylate in 20 ml of dioxane was admixed with 0.85 ml of a 40% solution of benzyl trimethylammonium hydroxide in water. The resulting solution was heated for 10 minutes at 75° C, then cooled, admixed with 5 N sodium hydroxide, and heated for one hour more. Then, the reaction mixture was cooled, acidified with concentrated hydrochloric acid, and the precipitate formed thereby was filtered off, washed with water, dried and recrystallized from a mixture of acetic acid and chloroform (1:9). The compound named in the heading, m.p. 242°-243° C, was obtained with a yield of 10.5 gm (99%) of theory).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US03987186 |
|---|
| Source dataset | uspto-grants-1976_10 |
|---|
| ORD ID | ord-c30e0f875f954764abcb2d9b3e7cb333 |
|---|
| Source note | uspto-grants-1976_10 |
|---|