Benzyl Alcohol → HCID 13907841, compound

HRID 255985Notes

Reaction equation

HRID 255985 reaction equation
Cl.[N+:2]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([O-:4])=[O:3].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].CCOCC.O>[CH2:12]([C:10]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:2]([O-:4])=[O:3])[CH:11]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 69462-NitroanilineHCID 14798Sodium Hydroxide

Product 1

HCID 13907841HCID 13907841, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3007855ZincchlorideSolvent

Procedure

To 20.4 parts of 36% w/w hydrochloric acid in which had previously been dissolved 13.4 parts of anhydrous zinc chloride are added 27.6 parts of o-nitro-aniline and 10.8 parts of benzyl alcohol. This mixture is stirred under reflux temperature for 6 hours and then poured into a hot solution of 50 parts of sodium hydroxide in 100 parts of water. After allowing the decomposed reaction mixtures to cool the organic phase is extracted with ether, and the ether solution washed with water, the ether evaporated and the residue distilled to give a fraction with boiling point 192°-8° C. at 0.4 millibars. This fraction after dilution with 40°-60° petroleum ether containing a little ether yields 4-benzyl-2-nitro-aniline m.p. 80°-3° C.

Workup

  1. temperatureunder reflux temperature for 6 hours
  2. customthe decomposed reaction mixtures
  3. temperatureto cool the organic phase
  4. extractionis extracted with ether
  5. washthe ether solution washed with water
  6. customthe ether evaporated
  7. distillationthe residue distilled
  8. customto give a fraction with boiling point 192°-8° C. at 0.4 millibars

Sources & evidence

ORD record
ord-a03f485509b64f8f921c20d7fcc3cdf6
Source dataset
uspto-grants-1987_10
Patent number
US04700003

Reaction notes

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