Salicylaldehyde → HCID 15550541, compound

HRID 2308359Notes

Reaction equation

HRID 2308359 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:25]([N:27]=[C:28]=[O:29])[CH3:26].OC1C=CC=CC=1C=O>CN(C=O)C>[CH2:25]([NH:27][C:28]([O:13][C:12]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]([CH:8]=[O:9])=[CH:10][C:11]=1[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:29])[CH3:26]

Participants

6

Reactant 4

HCID 6998SalicylaldehydeHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 15550541HCID 15550541, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (5 g, 20 mmol) in DMF (100 mL) was added triethylamine (3.5 mL, 25 mmol) and the solution was stirred for 15 min at room temperature. Ethyl isocyanate (1.95 mL, 25 mmol) was added and the reaction mixture was stirred for 2 h at room temperature until no more hydroxybenzaldehyde was detected by TLC (Rf=0.78 for product and 0.89 for starting material using 1:1 hexanes/EtOAc). The reaction solution was concentrated by azeotropic removal of DMF with water. The resulting suspension was filtered, washed with water and dried in a vacuum oven to afford 96% of the title compound as a light buff solid.

Workup

  1. concentrationThe reaction solution was concentrated by azeotropic removal of DMF with water
  2. filtrationThe resulting suspension was filtered
  3. washwashed with water
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-34fdcc5c69cb44869f678e2d5366ba35
Source dataset
uspto-grants-2004_12
Patent number
US06835754B2

Reaction notes

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