Ethylene Glycol → HCID 86761589, compound

HRID 1515782Notes

Reaction equation

HRID 1515782 reaction equation
[CH2:1]([S:3][C:4](=[O:17])[CH:5]([CH:11]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12]1)[C:6]([S:8][CH2:9][CH3:10])=[O:7])[CH3:2].[CH2:18](O)[CH2:19][OH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:9]([S:8][C:6](=[O:7])[CH:5]([CH:11]1[CH2:15][CH2:14][C:13]2([O:20][CH2:19][CH2:18][O:16]2)[CH2:12]1)[C:4]([S:3][CH2:1][CH3:2])=[O:17])[CH3:10]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 12917176HCID 12917176, compound

Product 1

HCID 86761589HCID 86761589, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-(3-oxo-cyclopentyl)-dithiomalonic acid di-S-ethyl ester (43.6 g, 0.159 mol), ethane-1,2-diol (49.3 g, 0.796 mol), p-toluenesulfonic acid (5.5 g, 0.032 mol) and benzene (500 mL) were heated to reflux and water was removed with a Dean-Stark trap. After 16 h, the mixture was quenched with water and saturated aqueous sodium bicarbonate, extracted with ethyl acetate, dried and concentrated to afford crude product. Purification by flash column chromatography (QingDao silica gel, 200-300 mesh, 5% ethyl acetate/hexanes) afforded 2-(1,4-dioxa-spiro[4.4]non-7-yl)-dithiomalonic acid di-S-ethyl ester as a white solid (47.0 g, 92%).

Workup

  1. temperaturewere heated
  2. temperatureto reflux
  3. customwater was removed with a Dean-Stark trap
  4. customthe mixture was quenched with water and saturated aqueous sodium bicarbonate
  5. extractionextracted with ethyl acetate
  6. customdried
  7. concentrationconcentrated
  8. customto afford crude product
  9. customPurification by flash column chromatography (QingDao silica gel, 200-300 mesh, 5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4fb3bc06bc9d443c9d446afe25e91c96
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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