4-Hydroxybenzaldehyde → 4-(Decyloxy)benzaldehyde

HRID 550960

Reaction equation

HRID 550960 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>CN(C=O)C>[CH2:17]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 163141-Iododecane

Product 1

HCID 1410684-(Decyloxy)benzaldehydeYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (732 mg, 6 mmol) in anhydrous DMF (13 ml), under nitrogen atmosphere, K2CO3 (1658 mg, 12 mmol), and, after 10 minutes, iododecane (1785 mg, 7.2 mmol) were added. The mixture was heated to reflux for 3 hours, then water was added and the product was extracted with CH2Cl2. The organic layers were washed with water and with NaCl saturated solution, dried with Na2SO4. After evaporation of the solvent, the crude product was purified by chromatography on silica gel (Petroleum ether/Ethyl acetate 11/1) and 1530 mg (yield 97%) of the pure product of the title were obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionthe product was extracted with CH2Cl2
  4. washThe organic layers were washed with water and with NaCl saturated solution
  5. dry with materialdried with Na2SO4
  6. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-5622910040e14b06866c53bd5c3df00f
Source dataset
uspto-grants-2011_05
Patent number
US07947674B2

Linked notes

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