Salicylaldehyde → 2-Undecyloxybenzaldehyde

HRID 2165475Notes

Reaction equation

HRID 2165475 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:10](Br)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCCCCC>[CH2:20]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10]

Participants

6

Reactant 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 127441-Bromoundecane

Product 1

HCID 156174952-Undecyloxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of salicylaldehyde (10.15 moles), undecylbromide (10.3 mmoles) and potassium carbonate (11.7 mmoles) in dimethylformamide (10 ml) is heated to 100° C. for 1 hour and then is cooled. The reaction mixture is taken up in hexane and is washed with 5 percent sodium hydroxide and brine. After treatment with anhydrous magnesium sulfate and charcoal, the volatiles are removed under vacuum and the residue is purified by flash chromatography to give the desired product.

Workup

  1. temperatureis cooled
  2. washis washed with 5 percent sodium hydroxide and brine
  3. customAfter treatment with anhydrous magnesium sulfate and charcoal, the volatiles are removed under vacuum
  4. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-b0705f8a26c045d5a8fe3636f6a0dbe8
Source dataset
uspto-grants-1990_07
Patent number
US04939279

Reaction notes

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