Ethylene Glycol → 1,4,8-Trioxaspiro[4.5]decane

HRID 1365731Notes

Reaction equation

HRID 1365731 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[CH2:8](O)[CH2:9][OH:10].C1(C)C(S(O)(=O)=O)=CC=CC=1>C1C=CC=CC=1>[O:10]1[C:4]2([CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[O:7][CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 69252-Methylbenzenesulfonic acidHCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 534405191,4,8-Trioxaspiro[4.5]decaneYield 81%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of tetrahydro-4-pyranone (10 g, 99.9 mmol), ethylene glycol (20 mL, 150 mmol) and catalytic toluene sulfonic acid was refluxed in benzene (120 mL) for 5 h. After cooling to room temp, the benzene layer was decanted from the dark oil in the bottom of the flask and was concentrated. The resulting oil was taken up in methylene chloride and shaken in a separatory funnel. The CH2Cl2 layer was decanted from the insoluble oil. The CH2Cl2 layer was concentrated to give the title compound as a pale yellow oil (11.62 g, 81% yield). 1H-NMR (300 MHz, CDCl3) δ: 3.91 (4H, s), 3.71 (4H, t, J=5.5 Hz), 1.68 (4H, t, J=5.7 Hz).

Workup

  1. customthe benzene layer was decanted from the dark oil in the bottom of the flask
  2. concentrationwas concentrated
  3. customThe CH2Cl2 layer was decanted from the insoluble oil
  4. concentrationThe CH2Cl2 layer was concentrated

Sources & evidence

ORD record
ord-82df24f340e54b769a39114b0d0c3620
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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