Ethylene Glycol → HCID 10782137, compound

HRID 566556Notes

Reaction equation

HRID 566556 reaction equation
C([Li])CCC.[CH2:6]([OH:9])[CH2:7][OH:8].Br[CH2:11][CH:12]=[C:13]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1>O>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)=[CH:12][CH2:11][O:8][CH2:7][CH2:6][OH:9])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 21266348HCID 21266348, compoundHCID 178418339Butyllithium

Product 1

HCID 10782137HCID 10782137, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of n-butyllithium in hexanes (15.0 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 for 0.5 h at room temperature. 3-Bromo-1,1-bis(4-chlorophenyl)-1-propene (13.0 g, 38 mmol, prepared similarly to the method described in Example 26) was added and the reaction mixture was stirred at room temperature for 72 h. The mixture was poured into water (100 ml) and extracted with ethyl acetate (2×75 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 ethyl acetate (3:2) as eluent provided 8.1 g (66%) of 2-(3,3-bis-(4-chlorophenyl)-2-propen-1-yloxy)ethanol.

Workup

  1. additionWhen addition
  2. additionwas added
  3. stirringthe reaction mixture was stirred at room temperature for 72 h
  4. extractionextracted with ethyl acetate (2×75 ml)
  5. dry with materialThe combined organic extracts was dried (Na2SO4)
  6. customthe solvent evaporated in vacuo
  7. additiona mixture of n-heptane and ethyl acetate (3:2) as eluent

Sources & evidence

ORD record
ord-c54ba29474784e5ca0499dcf738ac1c6
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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