Triethylene glycol monomethyl ether → HCID 44622260, compound

HRID 579376Notes

Reaction equation

HRID 579376 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][OH:11].[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH:13]=[CH2:14].C[O-].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:14][CH2:13][C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 8178Triethylene glycol monomethyl etherHCID 15458tert-Butyl acrylateHCID 10942334Sodium Methoxide

Product 1

HCID 44622260HCID 44622260, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethyleneglycol monomethyl ether (50 g, 304.5 mmol) was taken in tert-butyl acrylate (35.1 g, 274 mmol) and the mixture was stirred for 10 minutes. Sodium methoxide (1.97 g, 36.5 mmol) was added and stirred at ambient temperature for 8-10 hours. The reaction completion was checked by thin layer chromatography (TLC). The reaction mixture was diluted with ethyl acetate (200 mL) and the organic layer was washed with water, saturated brine solution and dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain tert-butyl 2,5,8,11-tetraoxatetradecan-14-oate (67 g, 75.3%).

Workup

  1. stirringstirred at ambient temperature for 8-10 hours
  2. washthe organic layer was washed with water, saturated brine solution
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a08bad9f57b14c9aaa7f1948196df3a7
Source dataset
uspto-grants-2015_05
Patent number
US09040723B2

Reaction notes

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