Propanal → HCID 13924084, compound

HRID 1789532Notes

Reaction equation

HRID 1789532 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 30 minutes. Then water (500 ml) is added over a period of 30 minutes and the reaction warmed to room temperature. The reaction is partitioned between ether (500 ml) and water. The aqueous layer is extracted with ether (2×500 ml) and the organic 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 30 minutes
  6. temperaturethe reaction warmed to room temperature
  7. customThe reaction is partitioned between ether (500 ml) and water
  8. extractionThe aqueous layer is extracted with ether (2×500 ml)
  9. washThe product is washed with brine (500 ml)
  10. dry with materialThe residue is dried over anhydrous magnesium sulfate
  11. filtrationthe solid filtered out
  12. customThe remaining solvent is removed
  13. customleaving a clear yellow oil
  14. distillationThe crude product is fractionally distilled under reduced pressure

Sources & evidence

ORD record
ord-1925490ceb67467592872507621e072d
Source dataset
uspto-grants-1987_08
Patent number
US04689349

Reaction notes

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