3,4-Dihydroxybenzaldehyde → 3-Hydroxy-4-pentyloxybenzaldehyde

HRID 2213563Notes

Reaction equation

HRID 2213563 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-].[Cs+].[Cs+]>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:14][CH2:11][CH2:3][CH2:2][CH2:9][CH3:8])[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 87683,4-DihydroxybenzaldehydeHCID 10796Cesium carbonate

Product 1

HCID 132247513-Hydroxy-4-pentyloxybenzaldehydeYield 48.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

n-Bromopentane (0.90 mL, 7.25 mmol, 1 eq) was added dropwise to a stirred solution of 3,4-dihydroxybenzaldehyde (1 g, 7.25 mmol, 1 eq) and cesium carbonate (7.07 g, 21.7 mmol, 3 eq) in N,N-dimethylformamide. The reaction mixture was stirred overnight and concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL), and the organic solution washed with water (2×50 mL), and brine (50 mL), then dried over magnesium sulfate and evaporated. Chromatography on silica with dichloromethane:petroleum ether (4:1) as eluent gave the product as a brown oil (367 mg, 24%). 1H NMR (CDCl3) δ 9.79 (s, 1H, O═C—H), 6.21 (s, 1H, OH), 4.08 (t, 2H, OCH2), 1.81 (m, 2H, OCH2CH2), 1.40 (m, 4H, CH2CH2CH3), 0.89 (t, 3H, CH3).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  3. washthe organic solution washed with water (2×50 mL), and brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-2851499243ca4b8195a16e049b58807c
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

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