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

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.53 g of 3-bromopropanol, 5.0 g of toluene and 0.05 g of n-dodecylpyridinium chloride 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 11 hours. In this period, 0.10 g of 3-bromopropanol and 0.10 g of a 27% aqueous sodium hydroxide solution were further added thereto at each time point of 4 and 7 hours. Then, the reaction mixture was cooled to 20° C. After 2.0 g of a 20% aqueous sulfuric acid solution and 5.0 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 1.3 g of 3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-propyl alcohol (purity: 85%, yield: 89%).

Provenance & Evidence