Benzyl Alcohol → Benzyl {o-[5-(2,4-dichlorophenoxy)-2-nitrophenoxy]phenoxy}acetate

HRID 21525Notes

Reaction equation

HRID 21525 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:16][C:17]1[CH:44]=[C:43]([Cl:45])[CH:42]=[CH:41][C:18]=1[O:19][C:20]1[CH:21]=[CH:22][C:23]([N+:38]([O-:40])=[O:39])=[C:24]([CH:37]=1)[O:25][C:26]1[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=1[O:28][CH2:29][C:30](Cl)=[O:31].O>O1CCCC1.C(Cl)Cl>[Cl:16][C:17]1[CH:44]=[C:43]([Cl:45])[CH:42]=[CH:41][C:18]=1[O:19][C:20]1[CH:21]=[CH:22][C:23]([N+:38]([O-:40])=[O:39])=[C:24]([CH:37]=1)[O:25][C:26]1[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=1[O:28][CH2:29][C:30]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:31]

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 8471TriethylamineHCID 19932413{o-[5-(2,4-Dichlorophenoxy)-2-nitrophenoxy]phenoxy}acetyl chloride

Product 1

HCID 54168481Benzyl {o-[5-(2,4-dichlorophenoxy)-2-nitrophenoxy]phenoxy}acetateYield 77.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl alcohol (0.8 mL, 7.73 mmol) and triethylamine (1 mL, 7.17 mmol) are added to a mixture of {o-[5-(2,4-dichlorophenoxy)-2-nitrophenoxy]phenoxy}acetyl chloride (1.12 g, 2.38 mmol) in tetrahydrofuran. The reaction mixture is stirred for twenty minutes, poured into water and extracted with ether. The combined organic extracts are washed sequentially with one molar hydrochloric acid, water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an oil. Column chromatography of the oil using silica gel and a hexanes in methylene chloride solution gives the title product as a yellow oil (1.0 g) which is identified by NMR spectral analyses.

Workup

  1. extractionextracted with ether
  2. washThe combined organic extracts are washed sequentially with one molar hydrochloric acid, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain an oil

Sources & evidence

ORD record
ord-747da01c1a934f2ca7eb9695b5039c16
Source dataset
uspto-grants-1995_06
Patent number
US05424280

Reaction notes

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