Propanal → HCID 13924084, compound

HRID 1722390Notes

Reaction equation

HRID 1722390 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]=[CH:7]1.[Mg].[CH:12](=[O:15])[CH2:13][CH3:14].O>O1CCCC1>[OH:15][CH:12]([CH2:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]=[CH:7]1

Participants

6

Reactant 4

HCID 527PropanalHCID 962WaterHCID 5462224MagnesiumHCID 13924083HCID 13924083, compound2×

Product 1

HCID 13924084HCID 13924084, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

All reactions are carried out under an inert atmosphere. 3-(4-Chlorobut-1-yl)cyclopentene {3-(4-chlorobutyl)cyclopentene} (43 g, 0.27 moles) is diluted in tetrahydrofuran (50 ml) and added dropwise to a stirred, refluxing solution of tetrahydrofuran (200 ml) containing granular magnesium (30 g, 1.25 moles). After the addition is complete and the resulting Grignard salt has formed the reaction is refluxed an additional 2 hours. The reaction vessel is then cooled in a 0° C. ice bath and propionaldehyde (15.6 g, 0.27 moles) diluted in tetrahydrofuran (20 ml) is added dropwise over a period of 30 minutes. Then water (500 ml) is added over 30 minutes and the reaction warmed to room temperature. The reaction is partitioned between ether (500 ml) and the organic phase separated. The aqueous layer is extracted with ether (2×500 ml) and the ether extracts are combined. The product is washed with brine (500 ml) and the solvent volume reduced under vacuum. The residue is dried over anhydrous magnesium sulfate and the solid filtered out. The remaining solvent is removed leaving a clear yellow oil. The crude product is fractionally distilled under reduced pressure leaving the desired product as a clear, colorless oil (52 g, 0.29 moles), BP 76° C./0.25 mm.

Workup

  1. additionadded dropwise to a stirred
  2. additionAfter the addition
  3. customthe resulting Grignard salt has formed the reaction
  4. temperatureis refluxed an additional 2 hours
  5. additionis added dropwise over a period of 30 minutes
  6. temperaturethe reaction warmed to room temperature
  7. customThe reaction is partitioned between ether (500 ml)
  8. customthe organic phase separated
  9. extractionThe aqueous layer is extracted with ether (2×500 ml)
  10. washThe product is washed with brine (500 ml)
  11. dry with materialThe residue is dried over anhydrous magnesium sulfate
  12. filtrationthe solid filtered out
  13. customThe remaining solvent is removed
  14. customleaving a clear yellow oil
  15. distillationThe crude product is fractionally distilled under reduced pressure

Sources & evidence

ORD record
ord-a23f765a303f41178f910c8edad69f73
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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