Potassium Iodide → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 327594Notes

Reaction equation

HRID 327594 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[OH-].[K+].[I-].[K+].[CH:16]1(Br)[CH2:20][CH2:19][CH2:18][CH2:17]1>C(O)C>[CH:16]1([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[O:10][CH3:11])[CH:5]=[O:6])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8728BromocyclopentaneHCID 12127IsovanillinHCID 14797Potassium Hydroxide

Product 1

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 54.9 g (0.36 mol) of 3-hydroxy-4-methoxybenzaldehyde in 400 mL of absolute ethanol was added 40.4 g (0.72 mol) of potassium hydroxide, 1.0 g (0.01 mol) of potassium iodide, and 77.0 mL (0.72 mol) of cyclopentyl bromide. The mixture was warmed to reflux for 48 hours at the end of which time the completed reaction was cooled to room temperature and concentrated to a syrup. The resulting residue was dissolved in 500 ml of ethyl acetate, washed with one, 100-mL portion of water, with one, 50-mL portion of dilute hydrochloric acid, with one, 100-mL portion of saturated sodium bicarbonate, and with one, 50-mL portion of saturated sodium chloride. The organic fraction was dried over sodium sulfate and concentrated to dryness. The amber syrup was liquid chromatographed over 500 g of silica gel using 20% ethyl ether in hexane as an eluent to provide the analytically pure oil upon drying in vacuo.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for 48 hours at the end of which time
  3. customthe completed reaction
  4. concentrationconcentrated to a syrup
  5. dissolutionThe resulting residue was dissolved in 500 ml of ethyl acetate
  6. washwashed with one, 100-mL portion of water, with one, 50-mL portion of dilute hydrochloric acid, with one, 100-mL portion of saturated sodium bicarbonate
  7. dry with materialThe organic fraction was dried over sodium sulfate
  8. concentrationconcentrated to dryness
  9. customchromatographed over 500 g of silica gel using 20% ethyl ether in hexane as an eluent
  10. customto provide the analytically pure oil
  11. customupon drying in vacuo

Sources & evidence

ORD record
ord-1dd026c617444cec87984ce7d97cf55b
Source dataset
uspto-grants-1993_12
Patent number
US05274002

Reaction notes

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