Triethylene Glycol → tert-Butyl 12-hydroxy-4,7,10-trioxadodecanoate

HRID 1402661Notes

Reaction equation

HRID 1402661 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH:7]=[CH2:8])([CH3:4])([CH3:3])[CH3:2].[OH:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19]>C1COCC1>[C:1]([O:5][C:6](=[O:9])[CH2:7][CH2:8][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8172Triethylene GlycolHCID 15458tert-Butyl acrylate

Product 1

HCID 3625858tert-Butyl 12-hydroxy-4,7,10-trioxadodecanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Na metal (catalytic) was added to a stirring solution of acrylic acid tert-butyl ester (6.7 mL, 46 mmol), and 2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethanol (20.7 g, 138 mmol) in THF (100 mL) at 0° C. and the mixture was stirred overnight. Solvent was removed and the remaining oil dissolved in EtOAc (100 mL). The organic layer was washed with water (3×50 mL), and dried over Na2SO4 and the solvent removed in vacuo to give an oil which corresponds to the title compound that would be used as is for the next step. (M+1)=279.

Workup

  1. customSolvent was removed
  2. dissolutionthe remaining oil dissolved in EtOAc (100 mL)
  3. washThe organic layer was washed with water (3×50 mL)
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed in vacuo
  6. customto give an oil which

Sources & evidence

ORD record
ord-2b9a6310420e42cb93cbb44bce74b81f
Source dataset
uspto-grants-2014_12
Patent number
US08912148B2

Reaction notes

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