Acetic Acid → 3-(2,2-Dichlorovinyloxy)-benzaldehyde

3(2,2-Dichlorovinyloxy)benzyl bromide (2.5 g) was carefully added to a stirred solution of hexamethylene tetramine (2.1 g) in carbon tetrachloride (20 ml) at the ambient temperature. After five minutes the precipitate was collected by filtration and washed with acetone. The solid thus obtained was added to aqueous acetic acid solution (50% by weight, 16 ml) and the mixture refluxed for one hour. A mixture of water (16 ml) and concentrated hydrochloric acid (4.5 ml) was then added and the mixture refluxed for a further 15 minutes. After cooling the mixture was extracted with chloroform, the extracts washed with water (twice), dried over anhydrous magnesium sulphate and the solvent removed by evaporation under reduced pressure to yield a residue of substantially pure 3(2,2-dichlorovinyloxy)benzaldehyde, identification of which was confirmed by infra-red and nuclear magnetic resonance spectroscopy.

1. filtrationAfter five minutes the precipitate was collected by filtration
2. washwashed with acetone
3. customThe solid thus obtained
4. temperaturethe mixture refluxed for one hour
5. additionwas then added
6. temperaturethe mixture refluxed for a further 15 minutes
7. temperatureAfter cooling the mixture
8. extractionwas extracted with chloroform
9. washthe extracts washed with water (twice),
10. dry with materialdried over anhydrous magnesium sulphate
11. customthe solvent removed by evaporation under reduced pressure

ORD record

ord-1360fee28e8d486c9617f7c00a835339

Source dataset

uspto-grants-1976_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03987079