Ethyl Acetate → HCID 178447882, compound

HRID 1646471Notes

Reaction equation

HRID 1646471 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1.O>[CH2:7]([C@H:10]1[CH2:11][CH2:12][C@H:13]([C:16]2[CH:24]=[CH:23][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=2)[CH2:14][CH2:15]1)[CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178447883HCID 178447883, compound

Product 1

HCID 178447882HCID 178447882, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a three-necked flask having a 1 l capacity was added lithium aluminum hydride (5.7 g, 0.15 mol), and cooled down to 0° C., followed by dropwise adding tetrahydrofuran (100 ml) and a solution of 4-(trans-4'-n-propylcyclohexyl)benzoyl chloride (53.0 g, 0.2 mol) in tetrahydrofuran (100 ml) in this order, agitating the mixture at room temperature for 3 hours, again cooling it down to 0° C., adding ethyl acetate (10 ml), water (10 ml) and 2N NaOH aqueous solution (10 ml) in this order, heating the mixture under reflux for 30 minutes, cooling the resulting material, filtering, adding saturated NaCl aqueous solution (100 ml) and ethyl acetate (100 ml), removing the aqueous layer, washing the resulting organic layer with water till the washing water became neutral, drying over anhydrous sodium sulfate, removing a drying agent, concentrating under reduced pressure, recrystallizing from heptane solvent and drying to obtain the captioned compound (35.8 g). Its structure was confirmed by NMR spectra.

Workup

  1. customInto a three-necked flask having
  2. temperatureagain cooling it down to 0° C.
  3. temperatureheating the mixture
  4. temperatureunder reflux for 30 minutes
  5. temperaturecooling the resulting material
  6. filtrationfiltering
  7. additionadding saturated NaCl aqueous solution (100 ml) and ethyl acetate (100 ml)
  8. customremoving the aqueous layer
  9. washwashing the resulting organic layer with water till the washing water
  10. dry with materialdrying over anhydrous sodium sulfate
  11. customremoving a drying agent
  12. concentrationconcentrating under reduced pressure
  13. customrecrystallizing from heptane solvent
  14. customdrying

Sources & evidence

ORD record
ord-14596ad17cd741afa9e9211ac1f96d61
Source dataset
uspto-grants-1993_01
Patent number
US05180519

Reaction notes

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