Water → HCID 21217001, compound

HRID 1586524Notes

Reaction equation

HRID 1586524 reaction equation
[C:1]1([C:7]2[C:12](C3C=CC=CC=3)=[C:11]([C:19](OCC)=[O:20])[CH:10]=[CH:9][C:8]=2[C:24](OCC)=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:10]([C:10]1[C:11]([CH2:19][OH:20])=[C:12]([C:2]2[CH:1]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:8]([CH2:24][OH:25])[CH:9]=1)[CH2:9][CH2:8][CH2:7][CH2:12][CH3:11]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21217004HCID 21217004, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21217001HCID 21217001, compoundYield 146.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl 2,3-diphenyl-1,4-benzenedicarboxylate (21.1 g, 46.0 mmol) in anhydrous THF (175 mL) was added dropwise with stirring over a 0.5 hour period to a suspension of lithium aluminum hydride (7.89 g, 208 mmol) in 350 mL of anhydrous THF at 0° C. This solution was stirred at room temperature for 1 hour and refluxed for 24 hours. The solution was then cooled and treated with: 1) 8 mL of water, added dropwise and stirred carefully for 0.25 hour, 2) 24 mL of 15% NaOH with stirring for an additional 0.25 h, and 3) 24 mL of water with additional stirring for 0.25 hour. The THF was evaporated and the resulting mixture was stirred for 12 hours with a 10% (v/v) H2SO4 solution. The product was filtered and recrystallized from aqueous ethanol to give a white solid (12.6 g, 73% yield): mp 136-7° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureThe solution was then cooled
  3. additionadded dropwise
  4. stirringstirred carefully for 0.25 hour
  5. customThe THF was evaporated
  6. stirringthe resulting mixture was stirred for 12 hours with a 10% (v/v) H2SO4 solution
  7. filtrationThe product was filtered
  8. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-d8258205bd7f47acbe0d08ce371c1d44
Source dataset
uspto-grants-1999_08
Patent number
US05945502

Reaction notes

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