HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Hydroxyacetophenone → 3-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Hydroxyacetophenone | HCID 8487 | — |
| Reactant | 2,3,4-Tri-o-acetyl-5-thioxylopyranosyl bromide | HCID 11382683 | — |
| Catalyst | Zincchloride | HCID 3007855 | — |
| Catalyst | Silver imidazolate | HCID 10931941 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside | HCID 15067852 | 14% |
Reaction Steps
If the procedure described in Preparation LXXXIII is followed starting from 3.45 g (25.3.10-3 mol) of 1-(3-hydroxyphenyl)ethanone, 6 g (16.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 3 g (17.10-3 mol) of silver imidazolate and 4.6 g (33.7.10-3 mol) of zinc chloride in 90 ml of methylene chloride and 30 ml of acetonitrile, 0.96 g (yield: 14%) of the expected product is obtained after purification by chromatography on silica gel using a toluene/ethyl acetate mixture (6/1 v/v) as the eluent, and crystallization from ether.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05246961 |
| Source dataset | uspto-grants-1993_09 |
| ORD ID | ord-fe312a64789d4aa28cb765688102371f |
| Source note | uspto-grants-1993_09 |