Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 1078313Notes

Reaction equation

HRID 1078313 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].C(=O)([O-])[O-].[K+].[K+].Br[CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C)C=O>[CH:19]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])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 8728Bromocyclopentane2×HCID 11430Potassium Carbonate2×HCID 12127Isovanillin

Product 1

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-hydroxy-4-methoxybenzaldehyde (100 grams (g hereinafter), 0.66 moles (mol hereinafter)), potassium carbonate (100 g, 0.73 mol) and bromocyclopentane (80 miliLiters (mL hereinafter), 0.79 mol) in dimethylformamide (0.5 Liters (L hereinafter)) was heated under an argon atmosphere at 100° Centigrade (C hereinafter). After 22 hours (h hereinafter), additional bromocyclopentane (10 mL, 0.1 mol) and potassium carbonate (20 g, 0.14 mol) were added and heating was continued for 24 h. The mixture was allowed to cool and was filtered. The filtrate was concentrated under reduced pressure and the residue was partitioned between ether and aqueous sodium carbonate. The organic extract was washed with aqueous sodium carbonate and dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 2:1 hexanes/ether to provide a pale yellow oil (121 g, 84%). Analysis Calc. for C13H16O3 :C 70.89, H 7.32; found: C 70.71, H 7.33.

Workup

  1. temperaturewas heated under an argon atmosphere at 100° Centigrade (C hereinafter)
  2. temperatureheating
  3. temperatureto cool
  4. filtrationwas filtered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was partitioned between ether and aqueous sodium carbonate
  7. extractionThe organic extract
  8. washwas washed with aqueous sodium carbonate
  9. dry with materialdried (potassium carbonate)
  10. customThe solvent was removed in vacuo
  11. customthe residue was purified by flash chromatography
  12. washeluting with 2:1 hexanes/ether

Sources & evidence

ORD record
ord-b5cbf8b5f80e4bca9796d12959a11a10
Source dataset
uspto-grants-1996_08
Patent number
US05547979

Reaction notes

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