Ethylene Glycol → 2-(3-(2-Methylphenyl)-3-phenyl-2-propen-1-yloxy)ethanol

HRID 566541Notes

Reaction equation

HRID 566541 reaction equation
C([Li])CCC.[CH2:6]([OH:9])[CH2:7][OH:8].Br[CH2:11][CH:12]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[CH3:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:12][CH2:11][O:8][CH2:7][CH2:6][OH:9]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 54536217HCID 54536217, compoundHCID 178418339Butyllithium

Product 1

HCID 539527602-(3-(2-Methylphenyl)-3-phenyl-2-propen-1-yloxy)ethanolYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of n-butyllithium in hexanes (13.0 ml, 2.5 M) was added dropwise under a nitrogen atmosphere to ethylene glycol (30 ml) at 10° C. When addition was complete the mixture was stirred 0.5 h at room temperature. 3-Bromo-1-(2-methylphenyl)-1-phenyl-1-propene (9.3 g, 32 mmol) was added and the reaction mixture was stirred at room temperature for 100 h. The mixture was poured into water (200 ml) and extracted with ethyl acetate (3×75 ml). The combined organic extracts was dried (Na2SO4) and the solvent evaporated in vacuo. Flash chromatography of the residue on silica gel (200 g) using a mixture of n-heptane and THF (4:1) as eluent provided 3.9 g (45%) of 2-(3-(2-methyl-phenyl)-3-phenyl-2-propen-1-yloxy)ethanol.

Workup

  1. additionWhen addition
  2. stirringthe reaction mixture was stirred at room temperature for 100 h
  3. extractionextracted with ethyl acetate (3×75 ml)
  4. dry with materialThe combined organic extracts was dried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. additiona mixture of n-heptane and THF (4:1) as eluent

Sources & evidence

ORD record
ord-1e6f8fd90895457a869e2c88261f8d72
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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