Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Pentyn-2-ol | HCID 92915 | — |
| Reactant | 1-(4-Bromophenyl)propan-2-one | HCID 736332 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Product | HCID 18353346 | HCID 18353346 | 90.3% |
Reaction Steps
0,35 g (0,5 mmol) Pd[TPP]2Cl2 and 0.12 g (=0.6 mmol) of copper(I) iodide and, with stirring in the course of a few minutes, 10.7 g (=0.13 mmol) of 1-methyl-3-butyn-1-ol are added to a solution of 21.3 g (=0.1 mol) of 4-bromophenylacetone in 250 ml of triethylamine. The mixture is warmed to 55° C. and the temperature is allowed slowly to rise to 80° C. during the course of 4 hours. After cooling, the mixture is filtered and the filtrate is concentrated. The oil which remains is chromatographed on silica gel. 17.4 g (90.3% of theory) of 4-(3-hydroxy-3-methyl-1-butynyl)phenylacetone are obtained; m.p. 67-69° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06319925B1 |
|---|
| Source dataset | uspto-grants-2001_11 |
|---|
| ORD ID | ord-001e0c8865ab414f8a62ce2c345515f4 |
|---|
| Source note | uspto-grants-2001_11 |
|---|
