Ethylene Glycol → HCID 54273351, compound

HRID 1384865Notes

Reaction equation

HRID 1384865 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][O:5][CH:4]([CH2:8][O:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:3]1.[CH2:22](O)[CH2:23][OH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.ClCCl>[O:24]1[C:2]2([CH2:7][CH2:6][O:5][CH:4]([CH2:8][O:9][S:10]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)(=[O:11])=[O:12])[CH2:3]2)[O:1][CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 54197444HCID 54197444, compound

Product 1

HCID 54273351HCID 54273351, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

4-Nitro-benzenesulfonic acid 4-oxo-tetrahydro-pyran-2-ylmethyl ester (0.5 g, 1.59 mmol), ethylene glycol (986 mg, 15.9 mmol) and p-toluene sulfonic acid (61 mg, 0.32 mmol) were refluxed in benzene (20 ml) for 20 hours. The solvent was removed in vacuo to afford a solid. The solid was dissolved in dichloromethane (30 ml) and successively washed with a saturated aqueous solution of sodium bicarbonate (2×5 ml) and water (2×5 ml). The organic phase was dried (Na2SO4), filtered and the solvent removal in vacuo afforded 582 mg (100%) of 4-nitro-benzenesulfonic acid 1,4,8-trioxa-spiro[4.5]dec-7-ylmethyl ester as a solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customto afford a solid
  3. washsuccessively washed with a saturated aqueous solution of sodium bicarbonate (2×5 ml) and water (2×5 ml)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removal in vacuo

Sources & evidence

ORD record
ord-a932bf5bdf524d44ad7033b84b822c6a
Source dataset
uspto-grants-2001_07
Patent number
US06262044B1

Reaction notes

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