Salicylaldehyde → HCID 136355291, compound

HRID 1803479Notes

Reaction equation

HRID 1803479 reaction equation
[CH2:1]([C@@H:8]([NH2:14])[CH:9]([O:12][CH3:13])[O:10][CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15](=O)[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[OH:18]>C1(C)C=CC=CC=1>[CH2:1]([CH:8]([N:14]=[CH:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[OH:18])[CH:9]([O:10][CH3:11])[O:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6998SalicylaldehydeHCID 44199594HCID 44199594, compound

Product 1

HCID 136355291HCID 136355291, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 50 ml three-necked flask equipped with a thermometer, a magnetic stirrer and a condenser, 0.14 g of optically enriched (R)-1-benzyl-2,2-dimethoxyethylamine (91% ee, determined by chiral HPLC) (0.71 mmol, 1 mol.eq.) and 0.09 g of salicylaldehyde (0.71 mmol, 1 mol.eq.) are introduced into 1 g of toluene. This medium is left to stir at ambient temperature for 2-3 h. After concentrating, a crude mass of 0.21 g of 2-[(1-benzyl-2,2-dimethoxyethylimino)methyl]phenol is obtained.

Workup

  1. waitThis medium is left
  2. concentrationAfter concentrating

Sources & evidence

ORD record
ord-940e1d4005964a348549b9d59e988dd9
Source dataset
uspto-grants-2013_01
Patent number
US08350092B2

Reaction notes

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