Triethylene glycol monobutyl ether → HCID 86661951, compound

HRID 1892020Notes

Reaction equation

HRID 1892020 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14])[CH2:2][CH2:3][CH3:4].CC([O-])(C)C.[K+].[C:21]([O:25]C(C)(C)C)(=[O:24])[CH:22]=[CH2:23]>C1(C)C=CC=CC=1>[C:21]([OH:25])(=[O:24])[CH2:22][CH2:23][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:1][CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8923Triethylene glycol monobutyl etherHCID 15458tert-Butyl acrylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86661951HCID 86661951, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To 4.13 g of triethylene glycol mono-n-butyl ether in toluene (150 mL) are added 264 mg of t-BuOK (potassium tert-butanolate) in portions and then 5.81 g of t-butyl acrylate in toluene (20 mL) at room temperature. The mixture is stirred at room temperature overnight, and toluene is removed in vacuo. To this residue are added 40 mL of 0.5 N KOH ethanol solution, and the reaction mixture is heated to reflux for 2 h (hours). After acidifying to pH 3 with diluted HCl aq. solution, EtOAc (ethyl acetate) is added to the mixture. The extract with EtOAc is concentrated, and the residue is applied to silica gel column with CH2Cl2-MeOH (methylene chloride-methanol) mixture as eluent. I1 is obtained as colorless oil, 5.34 g.

Workup

  1. customat room temperature
  2. customtoluene is removed in vacuo
  3. additionTo this residue are added 40 mL of 0.5 N KOH ethanol solution
  4. temperaturethe reaction mixture is heated
  5. temperatureto reflux for 2 h (hours)
  6. additionis added to the mixture
  7. extractionThe extract with EtOAc
  8. concentrationis concentrated
  9. customI1 is obtained as colorless oil, 5.34 g

Sources & evidence

ORD record
ord-1d83f9c3caea420d88a49c3a0855e0da
Source dataset
uspto-grants-2013_08
Patent number
US08507569B2

Reaction notes

Loading…