Sulfuric Acid → 3-[2,6-Dichloro-4-(3,3-dichloroallyloxy)-phenoxy]-propan-1-ol

Temperature

60 °C

A mixture of 0.53 g of 3-bromopropanol, 5.0 g of toluene and 0.06 g of tetra-n-butylammonium sulfate was heated to 60° C. Thereto was added dropwise a mixed solution of 1.0 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 5.0 g of water and 0.54 g of a 27% aqueous sodium hydroxide solution with stirring over 6 hours. After completion of the addition, the mixture was further stirred at 60° C. for 4 hours. Then 0.10 g of 3-bromopropanol and 0.10 g of a 27% aqueous sodium hydroxide solution were added thereto, and the mixture was further stirred for 10 hours. The reaction mixture was then cooled to 20° C. After 2.0 g of a 20% aqueous sulfuric acid solution and 4.3 g of toluene were added thereto, the mixture was stirred and then separated. The obtained organic layer was washed with 5.0 g of water and concentrated under reduced pressure to give 1.2 q of 3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-propyl alcohol (purity: 89%, yield: 91%).

1. additionAfter completion of the addition
2. stirringthe mixture was further stirred at 60° C. for 4 hours
3. stirringthe mixture was further stirred for 10 hours
4. temperatureThe reaction mixture was then cooled to 20° C
5. stirringthe mixture was stirred
6. customseparated
7. washThe obtained organic layer was washed with 5.0 g of water
8. concentrationconcentrated under reduced pressure

ORD record

ord-a56f1f306c12479dba4b4aa7511ab191

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07652177B2