Ethylene Glycol → HCID 10517034, compound

HRID 1614822Notes

Reaction equation

HRID 1614822 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][CH:24]=[CH:23][C:22]=1[CH3:27])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]>O>[CH3:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])=[CH:12][CH2:11][O:8][CH2:7][CH2:6][OH:9]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 212663063-Bromo-1,1-bis(2-methylphenyl)-1-propeneHCID 178418339Butyllithium

Product 1

HCID 10517034HCID 10517034, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of n-butyllithium in hexanes (14 ml, 2.5 M) was added dropwise under a nitrogen atmosphere to ethylene glycol (28 ml) at 0° C. When addition was complete the mixture was stirred 0.5 h at room temperature. 3-Bromo-1,1-bis(2-methylphenyl)-1-propene (10.5 g, 35 mmol, prepared in a similar way to the method described in Example 23) was added and the reaction mixture was stirred at room temperature for 12 h and at 70° C. for 24 h. Water (100 ml) was added and the mixture was extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried over magnesium sulphate and the solvent evaporated in vacuo. Flash chromatography of the residue on silica gel (250 g) using a mixture of n-heptane and ethyl acetate (10:1) as eluent provided 3.0 g (30%) of 2-(3,3-bis(2-methylphenyl)-2-propen-1-yloxy)ethanol.

Workup

  1. additionWhen addition
  2. additionwas added
  3. stirringthe reaction mixture was stirred at room temperature for 12 h and at 70° C. for 24 h
  4. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
  5. dry with materialThe combined organic extracts were dried over magnesium sulphate
  6. customthe solvent evaporated in vacuo
  7. additiona mixture of n-heptane and ethyl acetate (10:1) as eluent

Sources & evidence

ORD record
ord-d5339e26cf0c486fb0da7f5d62c8f0a5
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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