3-tert-Butyl-2-hydroxybenzaldehyde → HCID 136388725, compound

HRID 1965925Notes

Reaction equation

HRID 1965925 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][CH:10]=[C:7]([CH:8]=O)[C:6]=1[OH:13])([CH3:4])([CH3:3])[CH3:2].[C:14]([C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)#[CH:15]>C(O)C.C(O)(=O)C>[C:1]([C:5]1[CH:12]=[CH:11][CH:10]=[C:7]([CH:8]=[N:20][C:19]2[CH:21]=[CH:22][C:16]([C:14]#[CH:15])=[CH:17][CH:18]=2)[C:6]=1[OH:13])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 36786753-tert-Butyl-2-hydroxybenzaldehydeHCID 37600254-Ethynylaniline

Product 1

HCID 136388725HCID 136388725, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

3-tert-butyl salicylaldehyde (1) (0.70 g/3.93 mmol) and 4-ethynyl aniline (0.49 g/4.2 mmol) were dissolved in 100 ml of ethanol. Molecular sieves (3 Å, 15 g) and a few drops of glacial acetic acid were added and the mixture was stirred at room temperature for three days. After filtration over sodium sulphate and removal of the solvent, the residue was extracted several times with n-pentane. The solution was filtered again over sodium sulphate, and the solvent was removed. The title compound was obtained as a yellow powder. Yield: 43%.

Workup

  1. filtrationAfter filtration
  2. customover sodium sulphate and removal of the solvent
  3. extractionthe residue was extracted several times with n-pentane
  4. filtrationThe solution was filtered again over sodium sulphate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-21b81e8879ad45e68b356821b081f1c5
Source dataset
uspto-grants-2013_04
Patent number
US08420563B2

Reaction notes

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