3-Chlorophenol → 2-(3-Chlorophenoxy)ethylamine

HRID 232314Notes

Reaction equation

HRID 232314 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl.Cl[CH2:13][CH2:14][NH2:15]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:13][CH2:14][NH2:15]

Participants

5

Reactant 3

HCID 79333-Chlorophenol2×HCID 24758Sodium hydrideHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 142453312-(3-Chlorophenoxy)ethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 5.0 g (38.9 mmol) of 3-chlorophenol to a 0° C. suspension of 3.42 g (85.6 mmol, 2.2 eq., 60% by wt. in mineral oil) of sodium hydride in 100 mL of dry tetrahydrofuran. Once the 3-chlorophenol is dissolved add 9.93 g (85.6 mmol, 2.2 eq.) of 2-chloroethylamine hydrochloride and stir at room temperature for 17 hr. Concentrate the reaction mixture and partition between 200 mL of methylene chloride and 50 mL water. Dry the organic layer over Na2SO4 and concentrate in vacuo to obtain the title compound.

Workup

  1. concentrationConcentrate the reaction mixture
  2. custompartition between 200 mL of methylene chloride and 50 mL water
  3. dry with materialDry the organic layer over Na2SO4
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-4668de3f1d65416382b1ea5478d85b0c
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Reaction notes

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