4-Hydroxybenzaldehyde → p-Dodecyloxybenzaldehyde

HRID 2222747Notes

Reaction equation

HRID 2222747 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+].[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[CH2:27]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 2855718-Crown-6

Product 1

HCID 141069p-DodecyloxybenzaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Hydroxybenzaldehyde (5.0 g, 41 mmol, 1.0 equiv.), potassium carbonate (8.5 g, 61 mmol, 1.5 equiv.), dodecyl bromide (12.3 g, 49.2 mmol, 1.20 equiv.), and 18-crown-6 (1.0 g, 4.1 mmol, 0.10 equiv.) were placed in a flask with a magnetic stirring bar and a cooling column, and dissolved in 50 ml of acetone. The mixture was refluxed for 24 h. After cooling down, the mixture was filtered and concentrated in vacuo. The crude product was subjected to a column chromatography using CH2Cl2 to afford the product as pale yellow solid (10.3 g, 35.0 mmol, 87% yield). 1H NMR (400 MHz, CDCl3) δ: 9.85 (s, 1H), 7.83 (d, 2H, J=8.6 Hz), 7.00 (d, 2H, J=8.6 Hz), 4.05 (t, 2H, J=6.4 Hz), 1.80 (m, 2H), 1.27 (m, 18H), 0.89 (t, 3H, J=6.7 Hz); 13C NMR (500 MHz, CDCl3) δ: 191.0, 164.5, 132.2, 130.0, 115.0, 68.7, 32.2, 29.9, 29.8, 29.6, 29.3, 26.2, 22.9, 14.4; APCI-MS m/z 291.3 (M+).

Workup

  1. temperatureThe mixture was refluxed for 24 h
  2. temperatureAfter cooling down
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0dd8a6051c35432d8385e02765a40e55
Source dataset
uspto-grants-2008_05
Patent number
US07371887B2

Reaction notes

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