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

HRID 1614809Notes

Reaction equation

HRID 1614809 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 over sodium sulphate 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-methylphenyl)-3-phenyl-2-propen-1-yloxy)ethanol. TLC: rf=0.20 (SiO2 ; n-heptane/THF=7:3).

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 over sodium sulphate
  5. customthe solvent evaporated in vacuo
  6. additiona mixture of n- heptane and THF (4:1) as eluent

Sources & evidence

ORD record
ord-e7bfd1273ce14750bd5930ce3af27d3e
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

Loading…