Ethylene Glycol → HCID 68745996, compound

HRID 228282Notes

Reaction equation

HRID 228282 reaction equation
[CH:1]([Si:4]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1)([CH3:3])[CH3:2].CC1C=CC(S(O)(=O)=O)=CC=1.O.[CH2:32](O)[CH2:33][OH:34]>C1C=CC=CC=1>[O:11]1[CH2:32][CH2:33][O:34][CH:10]1[C:9]1[CH:12]=[CH:13][C:6]([O:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:14]([CH3:16])[CH3:15])[CH:17]([CH3:19])[CH3:18])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 11403212HCID 11403212, compound

Product 1

HCID 68745996HCID 68745996, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Heat at reflux a mixture of the aldehyde (2.1033 g, 7.55 mmol), p-TsOH.H2O (14.4 mg, 0.076 mmol), and ethylene glycol (4.2 mL, 75.5 mmol) in benzene (75 mL) overnight, while removing azeotropically the H2O formed. Cool and wash with 10% K2CO3 (2×50 mL) and brine which contains 10% K2CO3 (50 mL). Back-extract the aqueous layers with benzene and Et2O (100 mL each). Concentrate the combined organic layers after drying over Na2SO4 to afford (4-[1,3]dioxolan-2-yl-phenoxy)triisopropylsilane.

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. customwhile removing azeotropically the H2O
  4. customformed
  5. temperatureCool
  6. washwash with 10% K2CO3 (2×50 mL) and brine which
  7. extractionBack-extract the aqueous layers with benzene and Et2O (100 mL each)
  8. concentrationConcentrate the combined organic layers
  9. dry with materialafter drying over Na2SO4

Sources & evidence

ORD record
ord-28ae82e88ee54521b5b3fcfb6165b141
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

Loading…