Ethylene Glycol → HCID 69178869, compound

HRID 2055736Notes

Reaction equation

HRID 2055736 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([OH:15])[CH2:13][OH:14].O=[C:17]1[CH2:22][CH2:21][C:20]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)([C:23]#[N:24])[CH2:19][CH2:18]1>C1(C)C=CC=CC=1>[S:27]1[CH:28]=[CH:29][C:25]([C:20]2([C:23]#[N:24])[CH2:21][CH2:22][C:17]3([O:15][CH2:12][CH2:13][O:14]3)[CH2:18][CH2:19]2)=[CH:26]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 59658097HCID 59658097, compound

Product 1

HCID 69178869HCID 69178869, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Catalytic quantities of para-toluene sulfonic acid and ethyleneglycol (13.3 g: 0.21 mole) were added to 4-oxo-1-thiophen-3-yl-cyclohexanecarbonitrile (22 g; 0.107 mole) dissolved in toluene (500 ml). The reaction mixture was stirred for about 2 hours under reflux. On completion of the reaction (reaction monitored by thin layer chromatography), the toluene phase was separated, washed with sodium hydrogen carbonate solution (200 ml), dried (sodium sulfate) and concentrated under vacuum. 25 g 8-thiophen-3-yl-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (95%; colorless solid) were obtained.

Workup

  1. temperatureunder reflux
  2. customOn completion of the reaction (reaction monitored by thin layer chromatography)
  3. customthe toluene phase was separated
  4. washwashed with sodium hydrogen carbonate solution (200 ml)
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b80df91798b64b1ebce202f3cb459289
Source dataset
uspto-grants-2008_02
Patent number
US07332519B2

Reaction notes

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