HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sulfuric Acid → 6-(3-Chloro-phenyl)-2,2-dimethyl-[1,3]dioxin-4-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzoyl chloride, 3-chloro- | HCID 69252 | — |
| Reactant | Lithium Bromide | HCID 82050 | — |
| Reactant | 2,2-Bis(trimethylsilyl)propanedioate | HCID 22224580 | — |
| Solvent | Isopropenyl acetate | HCID 7916 | — |
| Product | 6-(3-Chloro-phenyl)-2,2-dimethyl-[1,3]dioxin-4-one | HCID 22224690 | — |
| Product | 3-Chlorobenzoylacetic acid | HCID 22224778 | — |
Reaction Steps
The 3-(3-chloro-phenyl)-3-oxo-propionic acid was prepared from 3-chlorobenzoyl chloride (11 mL, 85.7 mmol) and bis(trimethylsilyl)malonate (23.0 mL, 90.0 mmol) with Et3N (25 mL, 180 mmol) and LiBr (8.19 g, 94.3 mmol) in CH3CN at 0° C. according to general procedure H (method c1). The crude material (17.1 g) was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure J (method a). Obtained as a yellow-brown solid (8.0 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07018998B2 |
| Source dataset | uspto-grants-2006_03 |
| ORD ID | ord-3511003bdf48466a85907b8b443ef3c0 |
| Source note | uspto-grants-2006_03 |