Hydrochloric Acid → 3'-Chloropropiophenone

HRID 2308744Notes

Reaction equation

HRID 2308744 reaction equation
[Mg].II.[CH2:4](Br)[CH3:5].[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#N.Cl.C([O:19]CC)C>O>[Cl:7][C:8]1[CH:9]=[C:10]([C:11](=[O:19])[CH2:4][CH3:5])[CH:13]=[CH:14][CH:15]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 3283Diethyl Ether3×HCID 6332Ethyl BromideHCID 13015Benzonitrile, m-chloro-HCID 5462224Magnesium

Product 1

HCID 5871283'-Chloropropiophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.86 g (0.2 mol) of magnesium turnings, 30 ml of dry diethyl ether and a grain of iodine are placed in a one liter three-necked round-bottomed flask equipped with a condenser, a calcium chloride drying tube, a pressure equalizing funnel and a magnetic stirrer; the flask is purged with nitrogen, and 21.8 g (0.2 mol) of ethyl bromide in 30 ml of dry diethyl ether are then added. The mixture is then heated under reflux for one hour and left to cool. At ambient temperature, 16.51 g (0.12 mol) of 3-chlorobenzonitrile in 70 ml of dry diethyl ether are then added. A copious precipitate forms. The mixture is stirred overnight at ambient temperture and then cooled in an ice bath and hydrolysed by slowly adding 50 ml of water and then about 100 ml of 6N hydrochloric acid until the pH is acid. The mixture is stirred for one and a half hours and then extracted with ethyl acetate. The organic extract is then washed twice with water, dried and concentrated on a rotary evaporator. This gives 26 g of an orange oil, which is concentrated in vacuo to give about 18.2 g of ochre crystals of 3'-chloropropiophenone melting at about 40° C.

Workup

  1. customequipped with a condenser, a calcium chloride drying tube
  2. additionare then added
  3. temperatureThe mixture is then heated
  4. temperatureunder reflux for one hour
  5. waitleft
  6. temperatureto cool
  7. temperaturecooled in an ice bath
  8. stirringThe mixture is stirred for one and a half hours
  9. extractionextracted with ethyl acetate
  10. extractionThe organic extract
  11. washis then washed twice with water
  12. customdried
  13. concentrationconcentrated on a rotary evaporator
  14. concentrationThis gives 26 g of an orange oil, which is concentrated in vacuo

Sources & evidence

ORD record
ord-902fbf54239e4635b4818037a3292794
Source dataset
uspto-grants-1987_09
Patent number
US04690931

Reaction notes

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