4-Chlorophenol → 1-Chloro-4-(3-chloropropoxy)benzene

HRID 1160491Notes

Reaction equation

HRID 1160491 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:12][CH2:13][CH2:14][Cl:15].[Na+].[Br-]>O>[Cl:15][CH2:14][CH2:13][CH2:12][O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 253881Sodium Bromide

Product 1

HCID 126856101-Chloro-4-(3-chloropropoxy)benzeneYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 1 L flask provided with a stirrer was charged with 128.6 g (1.0 mol) of p-chlorophenol (available from Tokyo Chemical Industry Co., Ltd.), 52.0 g (1.3 mols) of sodium hydroxide (available from Wako Pure Chemical Industries Ltd.), 188.9 g (1.2 mols) of 1-bromo-3-chloropropane (available from Tokyo Chemical Industry Co., Ltd.) and 300 g of water. The content was maintained at 100° C. for 6 hours. Then the reaction liquid was cooled to room temperature, and deposited NaBr, produced by side reaction, was filtered off. The organic phase was separated and subjected to distillation under reduced pressure to give 179.2 g of the target p-(3-chloropropoxy)chlorobenzene (yield: 83%, purity: 95%).

Workup

  1. customA 1 L flask provided with a stirrer
  2. customThen the reaction liquid
  3. temperaturewas cooled to room temperature
  4. customproduced by side reaction
  5. filtrationwas filtered off
  6. customThe organic phase was separated
  7. distillationsubjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-3c529b40a634418792e0de28a64dcf9f
Source dataset
uspto-grants-2010_10
Patent number
US07816475B2

Reaction notes

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