Ethylene Glycol → tert-Butyl 3-(2-hydroxyethoxy)propanoate

HRID 446525Notes

Reaction equation

HRID 446525 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[CH:2]=[CH2:3].[CH2:10]([OH:13])[CH2:11][OH:12].[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:12][CH2:11][CH2:10][O:13][CH2:3][CH2:2][C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 15458tert-Butyl acrylate

Product 1

HCID 11263965tert-Butyl 3-(2-hydroxyethoxy)propanoateYield 22.4%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

tert-Butyl acrylate (5.72 mL, 39.0 mmol) was added to a mixture of ethylene glycol (2.42 g, 39.0 mmol), tetrabutylammonium bromide (377 mg, 1.17 mmol) and potassium hydroxide (77 mg; purity, 85%; 1.17 mmol), and the mixture was stirred at room temperature for 4 days. The reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1, v/v) to give the title compound (1.66 g; yield, 22%) as a colorless oily substance.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-909ffb20939142d2949200af9cdd258e
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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