Ethylene Glycol → 2-(3,3-Diphenyl-2-propen-1-yloxy)ethanol

HRID 566537Notes

Reaction equation

HRID 566537 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][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[C:14]1([C:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:12][CH2:11][O:8][CH2:7][CH2:6][OH:9])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 123465451,1'-(3-Bromoprop-1-ene-1,1-diyl)dibenzeneHCID 178418339Butyllithium

Product 1

HCID 108009482-(3,3-Diphenyl-2-propen-1-yloxy)ethanolYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of n-butyllithium in hexanes (7.3 ml, 2.5 M) was added drop-wise under a nitrogen atmosphere to ethylene glycol (20 ml) at 10° C. When addition was complete the mixture was stirred for 0.5 h at room temperature. 3-Bromo-1,1-diphenyl-1-propene (5.0 g, 18.3 mmol) was added and the reaction mixture was stirred at room temperature for 1 h, at 80° C. for 0.5 h and finally at room temperature for 3 h. Water (100 ml) was added and the mixture was extracted with ethyl acetate (100 ml). The phases were separated and the organic phase was washed with water (2×50 ml), dried (Na2SO4) and the solvent was evaporated in vacuo. Flash chromatography of the residue on silica gel (150 g) using n-heptane and THF (4:1) as eluent provided 2.9 g (62%) of 2-(3,3-diphenyl-2-propen-1-yloxy)ethanol.

Workup

  1. additionWhen addition
  2. stirringthe reaction mixture was stirred at room temperature for 1 h, at 80° C. for 0.5 h and finally at room temperature for 3 h
  3. extractionthe mixture was extracted with ethyl acetate (100 ml)
  4. customThe phases were separated
  5. washthe organic phase was washed with water (2×50 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-f867fddb3a2140d4953d45e8fb0626f0
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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