HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl vinyl ether → 3-Chloro-2-(1-ethoxyethoxy)propyl acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl vinyl ether | HCID 8023 | — |
| Reactant | 3-Chloro-2-hydroxypropyl acetate | HCID 98069 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-Chloro-2-(1-ethoxyethoxy)propyl acetate | HCID 13153905 | 98% |
Reaction Steps
A solution of 30.5 g (0.20 mol) of 3-chloro-2-hydroxy-1-propyl acetate (prepared in Example 1), 22 g (0.30 mol) of ethyl vinyl ether, and 7.5 g (0.030 mol) of pyridinium p-toluenesulfonate in 150 mL of methylene chloride was stirred at room temperature for 6 hours. The solution was then washed with 75 mL of water, dried and stripped of solvent in vacuo to give 44.0 g (98.0%) of 3-chloro-2-(1-ethoxyethoxy)-1-propyl acetate: 1H NMR (CDCl3) δ1.05-1.37 (overlapping t and d, 6H, --CH2CH3 and --CHCH3); 2.07 (s, 3H, --COCH); 3.53 and 4.12 (m. 7H, --CH2CHCH2 and --CH2CH3); 4.72 (q, J=4 Hz, 1H, --CHCH3); IR (film) 1740 cm-1 (--COCH3 ). The unpurified product was used in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04395561 |
| Source dataset | uspto-grants-1983_07 |
| ORD ID | ord-8927f2b97820461aaf0453cd3e4bdda9 |
| Source note | uspto-grants-1983_07 |