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

HRID 1994392Notes

Reaction equation

HRID 1994392 reaction equation
Br[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>[Cl-].C([N+]1C=CC=CC=1)CCCCCCCCCCC.C1(C)C=CC=CC=1.O>[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 123083-Bromo-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 108.2%

Reagents, catalysts & solvents 3

HCID 7717Dodecylpyridinium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

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%).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was further stirred at 60° C. for 11 hours
  3. waitIn this period
  4. customat each time point of 4 and 7 hours
  5. temperatureThen, the reaction mixture was cooled to 20° C
  6. stirringthe mixture was stirred
  7. customseparated
  8. washThe obtained organic layer was washed with 5.0 g of water
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-43b92d214f814dafbf1dfb90e3ee37e5
Source dataset
uspto-grants-2010_01
Patent number
US07652177B2

Reaction notes

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