2-Phenylethanol → 1-Nitro-3-(2-phenylethoxy)benzene

HRID 67796

Reaction equation

HRID 67796 reaction equation
CC(C)([O-])C.[K+].[N+]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)([O-])=O.[CH2:19]([OH:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN(C)P(N(C)C)(N(C)C)=O>O>[C:21]1([CH2:20][CH2:19][O:27][C:10]2[CH:11]=[C:12]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:14][CH:15]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 60542-PhenylethanolHCID 74521,3-DinitrobenzeneHCID 12679HexamethylphosphoramideHCID 23665647Potassium tert-butoxide

Product 1

HCID 130523131-Nitro-3-(2-phenylethoxy)benzeneYield 219.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium t-butoxide (11.2 g; 0.1 mol) is added under a nitrogen atmosphere to a stirred mixture of m-dinitrobenzene (16.8 g; 0.1 mol), phenethyl alcohol (12.2 g; 0.1 mol) and hexamethylphosphoramide (HMPA; 200 ml). Almost instantly a dark red color develops and then slowly fades in the course of the reaction and turns black. The reaction mixture is stirred for 7 days at room temperature. It is then drowned in water, and extracted twice with methylene chloride (500 ml). The methylene chloride solution is washed with water (3X), saturated brine (1X), dried over magnesium sulfate and evaporated to yield 53.5 g of a dark oil. Additional solvent (HMPA) and some m-dinitrobenzene is removed from the oil by heating same at about 90° C. under 0.5 mm vacuum. The residual oil (~25 g) is chromatographed on 1 kg silica gel with 3:1 hexane:methylene chloride. Collected fractions, containing the same material by thin layer chromatography, are combined and evaporated to afford 7.4 g (30%) of product, a light yellow oil. On standing, the oil crystallizes, mp. 46.5°-49° C.

Workup

  1. customslowly fades in the course of the reaction
  2. extractionextracted twice with methylene chloride (500 ml)
  3. washThe methylene chloride solution is washed with water (3X), saturated brine (1X)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-98a6af63fb1049dc8ef9e98988a49156
Source dataset
uspto-grants-1982_08
Patent number
US04346242

Linked notes

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