Diethylene Glycol → 4-(2-Thienyl)Butyric Acid

HRID 1057299Notes

Reaction equation

HRID 1057299 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[CH2:7][CH2:8][C:9]([OH:11])=[O:10].NN.C([O-])([O-])=O.[K+].[K+].C(O)COCCO>O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 9321HydrazineHCID 11430Potassium CarbonateHCID 783853-(2-Thenoyl)propionic acid

Product 1

HCID 783864-(2-Thienyl)Butyric AcidYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

3.6 g (0.019 mol) of 4-(2-thienyl)-4-keto-butyric acid, 2.74 ml (0.07 mol) of hydrazine 98%, 3.69 g (0.066 mol) of potash and 42 ml of diethylene glycol are placed in a two-necked flask equipped with a magnetic stirrer. The medium is heated for 7 h at 190° C. The medium is a clear uniform yellow. When it has cooled to room temperature it is hydrolysed with 200 ml of water. The diethylene glycol is extracted with 5 times 100 ml of ether. The aqueous phase is then acidified to pH 1 and extracted. The acid is absorbed in a solution of soda 5% washed with ether then acidified and absorbed for the last time in ether which is dried over MgSO4 and concentrated. 2.74 g of a clear yellow oil is obtained. Yield=85%.

Workup

  1. customequipped with a magnetic stirrer
  2. temperatureWhen it has cooled to room temperature it
  3. extractionThe diethylene glycol is extracted with 5 times 100 ml of ether
  4. extractionextracted
  5. customThe acid is absorbed in a solution of soda 5%
  6. washwashed with ether
  7. customabsorbed for the last time in ether which
  8. dry with materialis dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2f5e48f2d7dd49408f86cffc68d98423
Source dataset
uspto-grants-2003_02
Patent number
US06514967B1

Reaction notes

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