Triethylamine → 4-(4-Nitrophenoxy)phenyl 2-(4-(4-chlorophenoxy)phenoxy)propionate

HRID 1110664Notes

Reaction equation

HRID 1110664 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:18]=[CH:17][C:10]([O:11][CH:12]([CH3:16])[C:13](Cl)=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[N+:21]([C:24]1[CH:37]=[CH:36][C:27]([O:28][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=2)=[CH:26][CH:25]=1)([O-:23])=[O:22].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:18]=[CH:17][C:10]([O:11][CH:12]([CH3:16])[C:13]([O:35][C:32]3[CH:31]=[CH:30][C:29]([O:28][C:27]4[CH:36]=[CH:37][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=4)=[CH:34][CH:33]=3)=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1524504-(4-Nitrophenoxy)phenolHCID 129528252-(4-(4-Chlorophenoxy)phenoxy)propionic acid chloride

Product 1

HCID 144985654-(4-Nitrophenoxy)phenyl 2-(4-(4-chlorophenoxy)phenoxy)propionateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-(4-Chlorophenoxy)phenoxy)propionic acid chloride (0.6 g) and 4-(4-nitrophenoxy)phenol (0.5 g) were dissolved in dry tetrahydrofuran (10 ml), and the solution was stirred with an addition of triethylamine (0.3 ml) at room temperature for 2 hours. After completion of the reaction, the solvent was evaporated under a reduced pressure, the residue was dissolved in methylene chloride (20 ml), and washed with 1N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, water, and aqueous saturated sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was evaporated and the residue obtained was purified by medium pressure column chromatography to obtain 4-(4-nitrophenoxy)phenyl 2-(4-(4-chlorophenoxy)phenoxy)propionate (0.8 g)

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under a reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride (20 ml)
  4. washwashed with 1N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, water, and aqueous saturated sodium chloride
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customthe residue obtained
  8. customwas purified by medium pressure column chromatography

Sources & evidence

ORD record
ord-2e3a2c44b1124f1a983ae1dd4804c019
Source dataset
uspto-grants-1990_12
Patent number
US04976773

Reaction notes

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