Toluene → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 397625Notes

Reaction equation

HRID 397625 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH:18]1(Br)[CH2:22][CH2:21][CH2:20][CH2:19]1.C1(C)C=CC=CC=1>CN(C)C=O.[I-].[K+]>[CH:18]1([O:6][C:5]2[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=2[O:8][CH3:9])[CH:2]=[O:1])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeYield 80.5%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 100 g (0.66 mol) of isovanillin, 136.2 g (0.99 mol) of anhydrous potassium carbonate, and 3 g of potassium iodide in 650 ml of anhydrous dimethylformamide was stirred at 65° C. 127.3 g (0.85 mol) of cyclopentyl bromide was slowly added dropwise for 1 hour to the solution. This solution was stirred at 65° C. for 1 day and, then, its temperature was lowered to a room temperature. It was diluted by 2.0 L of toluene and was washed with 1M sodium hydroxide (2×1.5 L). The aqueous layer was extracted with 0.5 L of toluene, and the organic layer was washed with distilled water (2×1.5 L). The organic layer was dried and concentrated to obtain 117 g of light brown oily title compound. 1H NMR(CDCl3,d): 9.84(s, 1H) 7.42(m, 2H) 6.95(d, 1H, J=9 Hz) 4.87(m, 1H) 3.93(s, 3H) 2.1-6(m, 8H)

Workup

  1. customwas lowered to a room temperature
  2. washwas washed with 1M sodium hydroxide (2×1.5 L)
  3. extractionThe aqueous layer was extracted with 0.5 L of toluene
  4. washthe organic layer was washed with distilled water (2×1.5 L)
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e0c6ed9e7b1e44eab57367786f177a88
Source dataset
uspto-grants-2003_08
Patent number
US06610715B1

Reaction notes

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