Triethylene Glycol → 2-[2-(2-Propoxyethoxy)ethoxy]ethanol

HRID 511767Notes

Reaction equation

HRID 511767 reaction equation
[CH2:1]([OH:10])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][OH:9].[H-].[Na+].Br[CH:14](O)[CH2:15][CH3:16].C(OCC)(=O)C>O1CCCC1>[CH2:14]([O:10][CH2:1][CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][OH:9])[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 8172Triethylene GlycolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 12887879Bromopropanol

Product 1

HCID 113559922-[2-(2-Propoxyethoxy)ethoxy]ethanolYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethylene glycol (19.5 g, 0.13 mol) was dissolved in tetrahydrofuran (150 mL) and sodium hydride (2.60 g, 0.065 mol) was added portion wise over 0.5 h and the reaction was stirred for an additional 1 h. Then 1-bromopropanol (8.0 g, 0.065 mol) dissolved in tetrahydrofuran (30 mL) was added dropwise via addition funnel and the reaction was stirred overnight at room temperature. Crude reaction mixture was filtered through Celite, washed CH2Cl2, and evaporated to dryness. The resultant oil was dissolved in CH2Cl2 (250 mL), washed sat. NaCl (250 mL), H2O (250 mL), dried MgSO4, and evaporated to dryness. Column chromatography (Silica, ethyl acetate) afforded 1 a yellowish oil (2.24 g, 18% yield).

Workup

  1. additionwas added dropwise via addition funnel
  2. stirringthe reaction was stirred overnight at room temperature
  3. customCrude reaction mixture
  4. filtrationwas filtered through Celite
  5. washwashed CH2Cl2
  6. customevaporated to dryness
  7. dissolutionThe resultant oil was dissolved in CH2Cl2 (250 mL)
  8. washwashed sat. NaCl (250 mL), H2O (250 mL), dried MgSO4
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-d7bc363e6c114e469a6f138587d3436b
Source dataset
uspto-grants-2015_08
Patent number
US09101596B2

Reaction notes

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