Aniline → Salicylideneaniline

HRID 261825Notes

Reaction equation

HRID 261825 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C>[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 6998Salicylaldehyde

Product 1

HCID 136621Salicylideneaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

o-Hydroxybenzaldehyde (0.20 mole) is treated with aniline with vigorous stirring in a 1 l. Erlenmeyer Flask. After 15 mins., 33 cc of 95% ethanol is added and the reaction mixture is stirred vigorously for an additional 5 min. The reaction mixture is left standing at room temperature for 10 min., then it is placed in an ice-bath for 0.5 hr. The crystals which form are collected, washed with 95% ethanol, and air dried. Recrystallization from 85% ethanol yields N-(o-hydroxybenzylidene)aniline. m.p. 47°-49° C.

Workup

  1. stirringthe reaction mixture is stirred vigorously for an additional 5 min
  2. waitThe reaction mixture is left
  3. waitstanding at room temperature for 10 min.
  4. waitit is placed in an ice-bath for 0.5 hr
  5. customThe crystals which form are collected
  6. washwashed with 95% ethanol, and air
  7. customdried
  8. customRecrystallization from 85% ethanol

Sources & evidence

ORD record
ord-7068c5b62d684d64b685186bcf636c4e
Source dataset
uspto-grants-1979_05
Patent number
US04152452

Reaction notes

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