Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]- → HCID 22107237, compound

HRID 1456679Notes

Reaction equation

HRID 1456679 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[Na+].[CH:12]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O-:24])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[Na+].COCCOCCN(CCOCCOC)CCOCCOC>COCCOCCOC.[Cu]Cl>[CH:12]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 23663665Sodium o-chlorobenzoateHCID 23684558Sodium 2-cyclohexylphenolate

Product 1

HCID 22107237HCID 22107237, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8150DiglymeSolvent

Procedure

A mixture of 21.4 g (0.12 mol) of sodium 2-chlorobenzoate, 26.1 g (0.132 mol) of sodium 2-cyclohexylphenolate, 4.95 g (0.05 mol) of copper(I) chloride and 16.17 g (0.05 mol) of tris[2-(2-methoxyethoxy)-ethyl]amine (TDA) in 1.5 l of diethylene glycol dimethyl ether ("diglyme") is kept at 140° C. for 8 hours. The solvent is then concentrated on a vacuum rotary evaporator and the residue is diluted with water and acidified with concentrated hydrochloric acid. The product is extracted with ethyl acetate. The organic phases are washed with water, combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. 22.2 g (68%) of 2-(2-cyclohexylphenoxy)benzoic acid, melting point 109°-123° C., result as a beige powder.

Workup

  1. concentrationThe solvent is then concentrated on a vacuum rotary evaporator
  2. additionthe residue is diluted with water
  3. extractionThe product is extracted with ethyl acetate
  4. washThe organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated on a vacuum rotary evaporator

Sources & evidence

ORD record
ord-49ec1f354ccc45f8a5eda9c0f80c252a
Source dataset
uspto-grants-1998_12
Patent number
US05844024

Reaction notes

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