3,4-Dihydroxybenzaldehyde → 3,4-dihexyloxybenzaldehyde

HRID 270638Notes

Reaction equation

HRID 270638 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1O)[CH:5]=[O:6].[C:11]([O-:14])([O-])=O.[K+].[K+].I[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C(O)CCC>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:14][CH2:11][CH2:8][CH2:9][CH2:2][CH2:3][CH3:4])[CH:5]=[O:6])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 125271-Iodohexane

Product 1

HCID 118229373,4-dihexyloxybenzaldehydeYield 161%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

3,4-Dihydroxy-benzaldehyde (2.1 g, 0.015 mol), K2CO3 (4.0 g, 0.03 mol) and 1-iodohexane (6.4 g, 0.03 mol) were stirred in 100 ml of 1-butanol under reflux for 24 h. After cooling, the 1-butanol was removed by rotary evaporation. The residue was dissolved in 200 ml of ether, washed with water (dist.) and brine. The solution was dried over Na2SO4 and the solvent was removed to yield 3.7 g 3,4-Bis-hexyloxy-benzaldehyde (85%) as a dark solid. 1H NMR (400 MHz, CDCl3): δ 9.83 (s, 1H), 7.41 (m, 2H), 6.95 (d, 1H, J=8.5 Hz), 4.07 (m, 4H), 1.85 (m, 4H), 1.48 (m, 4H), 1.35 (m, 8H), 0.91 (m, 6H).

Workup

  1. temperatureunder reflux for 24 h
  2. temperatureAfter cooling
  3. customthe 1-butanol was removed by rotary evaporation
  4. dissolutionThe residue was dissolved in 200 ml of ether
  5. washwashed with water (dist.) and brine
  6. dry with materialThe solution was dried over Na2SO4
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-bca58000c6ac481aa891a9aacefb0a86
Source dataset
uspto-grants-2008_11
Patent number
US07449578B1

Reaction notes

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