Hydrochloric Acid → HCID 88658672, compound

HRID 652453Notes

Reaction equation

HRID 652453 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1O.[CH2:11]([CH:13]1O[CH2:14]1)[Cl:12].[OH-:16].[K+].Cl>C(O)C.O>[Cl:12][CH2:11][CH2:13][CH2:14][C:3]1[CH:4]=[CH:5][C:6]([C:8]#[N:9])=[C:7]2[O:16][C:2]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 2735739Benzonitrile, 3-chloro-4-hydroxy-

Product 1

HCID 88658672HCID 88658672, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

While a solution of 2-chloro-4-cyanophenol (50 g) and epichlorohydrin (60.3 g) in ethanol (55 ml) was refluxed, a solution of potassium hydroxide (21.9 g) in ethanol (90 ml) was added dropwise over a period of 40 minutes and the reaction mixture was further refluxed for 100 minutes. After the mixture was cooled, water (50 ml) was added thereto and it was neutralized with 1N hydrochloric acid. After the solvent was distilled off, the residue was extracted with diethyl ether. The extract was dried (over magnesium sulfate) and the diethyl ether was distilled off. The residue was distilled under reduced pressure to give 27 g of 3-chloro-4-(2,3-epoxy)propylbenzonitrile as a colorless oil. After crystallization, the crystals are recrystallized from isopropyl ether-ethyl acetate to give colorless needles. m.p. 71.0°-71.8° C.

Workup

  1. temperaturethe reaction mixture was further refluxed for 100 minutes
  2. temperatureAfter the mixture was cooled
  3. distillationAfter the solvent was distilled off
  4. extractionthe residue was extracted with diethyl ether
  5. dry with materialThe extract was dried (over magnesium sulfate)
  6. distillationthe diethyl ether was distilled off
  7. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-b2f8bba8dc834e3a82199112b1c1bfd9
Source dataset
uspto-grants-1987_06
Patent number
US04672073

Reaction notes

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