Diethylene Glycol → 2-(2,2-Dimethylpropyl)thiophene

HRID 235086Notes

Reaction equation

HRID 235086 reaction equation
C(O)COCCO.[OH-].[K+].[CH3:10][C:11]([CH3:20])([CH3:19])[C:12]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)=O.O.NN>Cl.O>[CH3:10][C:11]([CH3:20])([CH3:19])[CH2:12][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 27769762,2-Dimethyl-1-(thiophen-2-yl)propan-1-one

Product 1

HCID 5461892-(2,2-Dimethylpropyl)thiopheneYield 93.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To 45 mL of diethylene glycol was added 5.04 g (90 mmol) of KOH, and the mixture was stirred until solution was complete. To this was added 5.05 g (30 mmol) of 2.2-dimethyl-1-thiophenyl-1-propanone (Lancaster Chemical Co.), and 3.75 g of hydrazine monohydrate, and the reaction was stirred at reflux for 48 hours. The solution was cooled, diluted with 100 mL of 1N HCl and 100 mL of water, and extracted with pentane. The extract was dried over MgSO4, filtered and concentrated to give 4.31 g of the title product. NMR (CDCl3) δ:0.95 (s, 9H), 2.70 (s, 2H), 6.75 (dd, 1H, J=1, J=4 Hz), 6.98 (dd, 1H, J=4, J=6 Hz), 7.12 (dd, 1H, J=1, J=6 Hz).

Workup

  1. stirringthe reaction was stirred
  2. temperatureat reflux for 48 hours
  3. temperatureThe solution was cooled
  4. extractionextracted with pentane
  5. dry with materialThe extract was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bc20b6fa24a746c9ab7de8f7f4e5cc87
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Reaction notes

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