Salicylaldehyde → 2-Undecyloxybenzaldehyde

HRID 620535Notes

Reaction equation

HRID 620535 reaction equation
[H-].[Na+].[CH:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CN(C)C=O.CCCCCC>[CH2:22]([O:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[CH:3]=[O:11])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

6

Reactant 3

HCID 6998SalicylaldehydeHCID 127441-BromoundecaneHCID 24758Sodium hydride

Product 1

HCID 156174952-Undecyloxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirred suspension of sodium hydride (10.0 mmoles), which was prewashed with petroleum ether, in sieve dried dimethylformamide (10 ml) was added dropwise a solution of salicylaldehyde (10.1 mmoles) in dimethylformamide (1 ml). To the reaction mixture was then added undecyl bromide (10.0 mmoles) and the mixture stirred for 16 hours at ambient temperature under nitrogen. The reaction mixture was taken up in hexane (50 ml) and washed with 10 percent sodium hydroxide (2×50 ml) and saturated sodium chloride (50 ml). The organic phase was dried over anhydrous magnesium sulfate and charcoal. Evaporation of the volatiles yielded a colorless liquid which was purified by flash chromatography over silica gel with 2 percent ethyl acetate in hexane as eluant to afford the desired product as an oil.

Workup

  1. washwashed with 10 percent sodium hydroxide (2×50 ml) and saturated sodium chloride (50 ml)
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate and charcoal
  3. customEvaporation of the volatiles
  4. customyielded a colorless liquid which
  5. customwas purified by flash chromatography over silica gel with 2 percent ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-3b06caeacf0b413ab91829d53ec30855
Source dataset
uspto-grants-1989_04
Patent number
US04820719

Reaction notes

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