Hydrochloric Acid → Ethyl 4-[(4-fluorophenyl)methoxy]benzoate

HRID 1833924Notes

Reaction equation

HRID 1833924 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#N.[CH2:18]([OH:20])[CH3:19].Cl.CC[O:24]CC>>[CH2:18]([O:20][C:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[O:24])[CH3:19]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3283Diethyl EtherHCID 2243494Benzonitrile, 4-[(4-fluorophenyl)methoxy]-

Product 1

HCID 12398529Ethyl 4-[(4-fluorophenyl)methoxy]benzoate

Procedure

A solution of 4-cyanophenoxy-(4'-fluorophenyl) methane (2.25g.; 0.1 mole) in dry ether (20ml) with ethanol (0.46g.; 0.1 mole) was cooled in an ice-bath and then saturated with dry hydrogen chloride gas then allowed to stand for 24 hrs. The resulting solid was filtered off and dried, m.p. 210° C (rearrangement at 135° C). The imino-ether (1.54g) was dissolved in water (30ml) neutralised with dilute sodium hydroxide solution then boiled under reflux for 3 hrs. Mixture cooled and the product extracted with ether to give 4-ethoxycarbonylphenoxy-(4'-fluorophenyl) methane m.p. 60°-2° C.

Workup

  1. filtrationThe resulting solid was filtered off
  2. customdried
  3. customm.p. 210° C (rearrangement at 135° C)
  4. dissolutionThe imino-ether (1.54g) was dissolved in water (30ml)
  5. temperatureunder reflux for 3 hrs
  6. temperatureMixture cooled
  7. extractionthe product extracted with ether

Sources & evidence

ORD record
ord-3780997590a8493b8aca0057c59cad08
Source dataset
uspto-grants-1978_01
Patent number
US04067892

Reaction notes

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