4-Bromophenol → HCID 58969114, compound

HRID 1160494Notes

Reaction equation

HRID 1160494 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([Br:8])[CH:2]=1.[OH-].[Na+].[Cl:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[K+].[Br-]>O>[Cl:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:7][C:6]1[CH:5]=[CH:4][C:3]([Br:8])=[CH:2][CH:1]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 14798Sodium HydroxideHCID 805161-Bromo-6-chlorohexaneHCID 253877Potassium Bromide

Product 1

HCID 58969114HCID 58969114, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 1 L flask provided with a stirrer was charged with 173.0 g (1.0 mol) of p-bromophenol (available from Tokyo Chemical Industry Co., Ltd.), 84.2 g (1.5 mols) of sodium hydroxide (available from Wako Pure Chemical Industries Ltd.), 399.0 g (2.0 mols) of 1-chloro-6-bromohexane (available from Wako Pure Chemical Industries Ltd.) and 200 g of water. The content was maintained at 100° C. for 6 hours. Then the reaction liquid was cooled to room temperature, and deposited KBr, produced by side reaction, was filtered off. The organic phase was separated and subjected to distillation under reduced pressure to give 236.9 g of the target p-(6-chlorohexyloxy)bromobenzene (yield: 78%, purity: 96%).

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-1d96ab8ba4ae46f997ccd57944f657e2
Source dataset
uspto-grants-2010_10
Patent number
US07816475B2

Reaction notes

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