Ethylene Glycol → HCID 68960487, compound

HRID 1875683Notes

Reaction equation

HRID 1875683 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.C[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:21]([OH:24])[CH2:22][OH:23]>O>[CH3:1][C:14]([O:23][CH2:22][CH2:21][OH:24])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:13]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 12500beta-Methylstyrene

Product 1

HCID 68960487HCID 68960487, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A catalytic amount of either p-toluene sulfonic acid.H2O or Bio-Rad SCX resin (analytical grade, 5.1 meq/g, AG 50W-X8) was added to -methylstyrene (0.5 mL, 3.85 mmol) and ethylene glycol (0.21 mL, 3.85 mmol), and the reaction was stirred at rt for 5 days. The reaction mixture was loaded directly onto a SPE cartridge (10 g silica) and eluted with the following 10 mL fractions: 10% EtOAc/hexanes (fractions 1, 2), 30% EtOAc/hexanes (fractions 3, 4), and 50% EtOAc/hexanes (fractions 5, 6) to give the title compound (30.5 mg, 4%) for both conditions. The product was characterized by 1H NMR (400 MHz) in CDCl3.

Workup

  1. washeluted with the following 10 mL fractions

Sources & evidence

ORD record
ord-5e3769e79e3e4ebb989ac767bba65a19
Source dataset
uspto-grants-2012_11
Patent number
US08309572B2

Reaction notes

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