p-Toluenesulfonic acid → Norletimol

HRID 1279050Notes

Reaction equation

HRID 1279050 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:10]([N:17]=[CH:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[OH:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6998SalicylaldehydeHCID 7504Benzylamine

Product 1

HCID 71643Norletimol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5.0 mL of 2-hydroxy-benzaldehyde, 6.3 mL of benzylamine and 0.05 g of p-toluenesulphonic acid was refluxed in toluene for 2 hours using a Dean-Stark trap to remove liberated water. The volatiles were removed in vacuo yielding 10.1 g of crude 2-(benzylimino-methyl)-phenol.

Workup

  1. customto remove liberated water
  2. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-696de05f6c3a4ea4b5110db9d813a8de
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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