Sulfuric Acid → 3-(4-(3,3-Dichloro-2-propenyloxy)phenoxy)-1-propyl alcohol

HRID 1994394Notes

Reaction equation

HRID 1994394 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]([Cl:18])=[CH:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[OH-].[Na+].S(=O)(=O)(O)O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[Cl:6][C:7]([Cl:18])=[CH:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:2][CH2:3][CH2:4][OH:5])=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 123083-Bromo-1-propanol2×HCID 14798Sodium Hydroxide2×HCID 111720144-(3,3-Dichloro-2-propenyloxy)phenol

Product 1

HCID 866330383-(4-(3,3-Dichloro-2-propenyloxy)phenoxy)-1-propyl alcoholYield 98.8%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 1.40 g of 3-bromopropanol, 10.0 g of toluene and 0.14 g of tetra-n-butylammonium bromide was heated to 60° C. Thereto was added dropwise a mixed solution of 2.0 g of 4-(3,3-dichloro-2-propenyloxy)phenol, 10.0 g of water and 1.49 g of a 27% aqueous sodium hydroxide solution with stirring over 6 hours. After completion of the addition, the mixture was further stirred for 11 hours at 60° C. In this period, 0.20 g of 3-bromopropanol and 0.20 g of a 27% aqueous sodium hydroxide solution were further added at the time point of 7 hours. Then, the reaction mixture was cooled to 20° C. After 4.0 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 once with 10.0 g of a 1% aqueous sodium hydroxide solution and once with 10.0 g of water, and concentrated under reduced pressure to give 2.5 g of 3-(4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-propyl alcohol (purity: 93%, yield: 93%).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was further stirred for 11 hours at 60° C
  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 once with 10.0 g of a 1% aqueous sodium hydroxide solution and once with 10.0 g of water
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-38d71269f14b49ab84f60206520d7f8a
Source dataset
uspto-grants-2010_01
Patent number
US07652177B2

Reaction notes

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