Water → HCID 12073914, compound

HRID 2268108Notes

Reaction equation

HRID 2268108 reaction equation
[C:1]([C:5]1[C:6]([OH:17])=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[H][H].O>CN(C)C=O>[C:1]([C:5]1[C:6]([O:17][CH2:2][CH2:1][CH2:5][CH3:12])=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6880233,5-Di-tert-butylsalicylaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 12073914HCID 12073914, compoundYield 217.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

4.0 g of 3,5-di-tert.-butyl-2-hydroxybenzaldehyde (CAS # 37942-07-7) was dissolved in dimethylformamide (DMF). This was treated with 0.89 g of sodium hydride (50% in oil suspension) and stirred at 25° C. until hydrogen was no longer evolved. To this was added 2.01 ml n-bromobutane and the mixture was heated to 85° C. for 14 hr. This was cooled and poured into water. The aqueous was extracted with ether. The ether layer was washed with water, dried (MgSO4), and solvent was removed. Purification was accomplished by florsil column chromatography (15% ether/hexane) to give 5.4 g of 3,5-di-tert.-butyl-2-butyloxybenzaldehyde; 1H NMR (CDCl3) δ 10.31 (s, 1H,aldehyde), 7.70 (dd,4H,aromatics), 3.94 (t,2H,—OCH2—).

Workup

  1. temperatureThis was cooled
  2. extractionThe aqueous was extracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried (MgSO4), and solvent
  5. customwas removed
  6. customPurification

Sources & evidence

ORD record
ord-0487af8a04994735a385aa886345357d
Source dataset
uspto-grants-2001_12
Patent number
US06326397B1

Reaction notes

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