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

HRID 1994393Notes

Reaction equation

HRID 1994393 reaction equation
Cl[CH2:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH:15]=[C:16]([Cl:18])[Cl:17])[CH:10]=[C:9]([Cl:19])[C:8]=1[OH:20].[OH-].[Na+].S(=O)(=O)(O)O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1(C)C=CC=CC=1>[Cl:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH:15]=[C:16]([Cl:18])[Cl:17])[CH:10]=[C:9]([Cl:19])[C:8]=1[O:20][CH2:2][CH2:3][CH2:4][OH:5]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 123133-Chloro-1-propanol2×HCID 14798Sodium Hydroxide2×HCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Product 1

HCID 113139803-[2,6-Dichloro-4-(3,3-dichloroallyloxy)-phenoxy]-propan-1-olYield 83.2%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

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%).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was further stirred at 80° C. for 20 hours
  3. waitIn this period
  4. temperatureThen, the reaction mixture was 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

Sources & evidence

ORD record
ord-c3b0860b6d2547de8422ff7efb713dce
Source dataset
uspto-grants-2010_01
Patent number
US07652177B2

Reaction notes

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