Salicylaldehyde → 2-Undecyloxybenzaldehyde

HRID 2351049Notes

Reaction equation

HRID 2351049 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-fdff8d8120af4f5d8d745b58150f4553
Source dataset
uspto-grants-1989_10
Patent number
US04871771

Reaction notes

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