4-Hydroxybenzaldehyde → p-(Octyloxy)benzaldehyde

HRID 898186Notes

Reaction equation

HRID 898186 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][CH3:24]>C(#N)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][CH3:24]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 123801-Iodooctane

Product 1

HCID 90358p-(Octyloxy)benzaldehydeYield 848.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Hydroxybenzaldehyde (1.00 g, 0.82 mmol), potassium carbonate (1.70 g, 12.28 mmol) and 1-iodooctane (2.16 g, 9.00 mmol) were heated together in acetonitrile at 80° C. for 16 h. The reaction was cooled, filtered and concentrated. Silica gel chromatography eluting with hexane/ethyl acetate (20:1) gave a colorless oil (1.63 g): 1H NMR (500 MHz) δ 9.99 (s, 1H), 7.44-7.46 (m, 2H), 7.40 (s, 1H), 7.19 (m, 1H), 4.01 (t, J=6.6 Hz, 2H), 1.80 (m, 2H), 1.42-1.50 (m, 2H), 1.24-1.39 (m, 8H), 0.89 (t, J=6.9 Hz, 3H).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. washSilica gel chromatography eluting with hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-8f6925dc98ad4f3dac4f5d79751b6c4f
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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