Ethylene Glycol → 2-(4-Chlorophenyl)butanoic acid

HRID 1287580Notes

Reaction equation

HRID 1287580 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9]C(O)=O)=O)=[CH:4][CH:3]=1.[OH-:15].[K+].NN.Cl.[CH2:20]([OH:23])CO>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([CH2:8][CH3:9])[C:20]([OH:23])=[O:15])=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 776043-(4-Chlorobenzoyl)propionic acid

Product 1

HCID 346582-(4-Chlorophenyl)butanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A 5-liter, 3-neck flask is charged with 400 g (1.9 moles) of (I), 350 g potassium hydroxide, 2.47 liters of ethylene glycol and 155 g of 95% hydrazine diluted to 250 ml with water. The mixture is refluxed for 1.5 hours, after which the water is drained from the condenser and the internal temperature of the reaction mixture is allowed to rise to 190°. Refluxing is then continued for another 4 hours. The cooled solution is diluted with 2.5 liters of water and poured slowly into 2.0 liters of 6N hydrochloric acid. The precipitate is filtered and air-dried. Yield: 332.5 g, 88.1%, mp 54°-57°.

Workup

  1. temperatureThe mixture is refluxed for 1.5 hours
  2. customto rise to 190°
  3. temperatureRefluxing
  4. filtrationThe precipitate is filtered
  5. customair-dried

Sources & evidence

ORD record
ord-3fe6d79505ee4dca9ab3cc16cce4d4c5
Source dataset
uspto-grants-1976_10
Patent number
US03985731

Reaction notes

Loading…