Ethylene Glycol → HCID 68960487, compound

HRID 1724995Notes

Reaction equation

HRID 1724995 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.O.C[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:22]([OH:25])[CH2:23][OH:24]>>[CH3:1][C:15]([O:24][CH2:23][CH2:22][OH:25])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:14]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 12500beta-MethylstyreneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 68960487HCID 68960487, compoundYield 4%

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-6b8fa854babd4ffdb9134295dbf73293
Source dataset
uspto-grants-2009_02
Patent number
US07488827B2

Reaction notes

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