Ethylene Glycol → HCID 12426260, compound

HRID 1924479Notes

Reaction equation

HRID 1924479 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[CH2:12]([OH:15])[CH2:13][OH:14].[C:16]([O-:19])(O)=O.[Na+].[C:21]1(C)C=CC=CC=1>>[O:14]1[CH2:13][CH2:12][O:15][C:3]21[CH2:4][CH:5]1[CH2:6][CH:1]([CH2:11][C:16](=[O:19])[CH2:21]1)[CH2:2]2

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 12426260HCID 12426260, compound

Procedure

p-Toluenesulfonic acid (0.29 g, 1.51 mmol) was added to a solution of ketone (VII-l) (2.30 g, 15.11 mmol) in ethylene glycol (3.75 g, 60.45 mmol)—toluene (75 mL) and the reaction mixture was refluxed for 2 h using a Dean-Stark apparatus. The reaction mixture was allowed to cool to RT and was poured into a saturated solution of NaHCO3 (100 mL). The mixture was extracted with EtOAc (3×150 mL), dried (MgSO4) and concentrated. The crude product was purified by SGC using EtOAc:hexane=3:1 (v/v) as the eluent to give (VII-m) (2.33 g, 78%) as a white solid; 1H NMR (400 MHz, CDCl3) δ 1.68-1.84 (m, 6H), 2.26-2.34 (dd, J=6.6 and 18.4 Hz, 2H), 2.40-2.48 (m, 4H), 3.77-3.81 (m, 2H), 3.85-3.89 (m, 2H).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. extractionThe mixture was extracted with EtOAc (3×150 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by SGC
  6. customhexane=3:1 (v/v) as the eluent to give (VII-m) (2.33 g, 78%) as a white solid

Sources & evidence

ORD record
ord-5e50f365a5304726a77e7d82421e41b8
Source dataset
uspto-grants-2012_05
Patent number
US08178552B2

Reaction notes

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