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

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.37 g of 3-chloropropanol, 5.0 g of toluene and 0.06 g of tetra-n-butylammonium iodide was heated to 80° 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 0.51 g of a 27% aqueous sodium hydroxide solution with stirring over 6 hours. After completion of the addition, the mixture was further stirred at 80° C. for 20 hours. In this period, 0.20 g of 3-chloropropanol was further added at each time point of 7, 9, 12 and 17 hours, and 0.20 g of a 27% aqueous sodium hydroxide solution was further added at each time point of 12 and 17 hours. Then, the reaction mixture was cooled to 20° C. After 2.0 g of a 20% aqueous sulfuric acid solution was 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 1.0 g of 3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-propyl alcohol (purity: 87%, yield: 73%).

Provenance & Evidence