Ethylene Glycol → HCID 68199694, compound

HRID 1184415Notes

Reaction equation

HRID 1184415 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@@H:7]1[CH2:12][C:11](=[O:13])[CH2:10][CH2:9][C@H:8]1[C:14]([OH:16])=[O:15].[CH2:18](O)[CH2:19][OH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1COCC1>[CH3:17][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]1[C@H:8]([C:14]([OH:16])=[O:15])[CH2:9][CH2:10][C:11]2([O:20][CH2:19][CH2:18][O:13]2)[CH2:12]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 86692737HCID 86692737, compound

Product 1

HCID 68199694HCID 68199694, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1R,2R)-2-(o-tolyl)-4-oxo-cyclohexanecarboxylic acid (500 mg, 2.153 mmol) in THF (6.0 ml) was reacted with ethylene glycol (0.600 ml, 10.76 mmol) and p-toluenesulfonic acid (82 mg, 0.431 mmol), and then aged at rt until the reaction was complete. The mixture was poured into water and extracted with EtOAc. The combined organic portions were dried (Na2SO4), filtered and concentrated to afford the title compound. HPLC/MS: 231.0 (M-CO2H+1), Rt=1.04 min (LC-2).

Workup

  1. customaged at rt until the reaction
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic portions were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b78f7e05f98c4631b02ec1e7f6f49105
Source dataset
uspto-grants-2014_03
Patent number
US08669252B2

Reaction notes

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