Water → 1,3,5-Benzenetrimethanol

HRID 2225050Notes

Reaction equation

HRID 2225050 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[C:8]1[C:13]([C:14]([O-])=[O:15])=[C:12](C)[C:11]([C:18]([O-])=[O:19])=[C:10](C)[C:9]=1[C:22]([O-])=[O:23].O.[OH-].[Na+]>C1COCC1>[OH:15][CH2:14][C:13]1[CH:12]=[C:11]([CH2:18][OH:19])[CH:10]=[C:9]([CH2:22][OH:23])[CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 7055060Trimethyl-1,3,5-benzenetricarboxylateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 27480481,3,5-BenzenetrimethanolYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 3-liter, round-bottom flask equipped with an overhead stirrer, an addition funnel and a reflux condenser was charged with lithium aluminum hydride (49.7 grams, 1.31 mol) and anhydrous THF (500 ml) under nitrogen atmosphere. The resulting suspension was slowly heated to reflux and a solution of trimethyl-1,3,5-benzenetricarboxylate (100.0 grams, 0.40 mol) in anhydrous THF (1.0 liter) was added dropwise thereto while maintaining a gentle reflux (3 hours). The resulting gray suspension was stirred under reflux for additional 7 hours and then cooled in an external ice-water bath. The excess lithium aluminum hydride was hydrolyzed by dropwise addition of water (50 ml, 45 minutes), then 15% NaOH (50 ml, slow stream), and finally more water (150 ml, slow stream). The resulting suspension was stirred at ambient temperature for 14 hours. The solids were filtered off and the filtrate was concentrated under high vacuum to obtain a colorless oil which slowly solidified to afford 1,3,5-tris(hydroxylmethyl)benzene (62.3 grams, 94%) as a white solid. The 1H NMR and 13C NMR spectra were consistent with the assigned structure.

Workup

  1. customA 3-liter, round-bottom flask equipped with an overhead stirrer, an addition funnel and a reflux condenser
  2. temperatureThe resulting suspension was slowly heated
  3. temperatureto reflux
  4. temperaturewhile maintaining
  5. temperaturea gentle reflux (3 hours)
  6. temperatureunder reflux for additional 7 hours
  7. temperaturecooled in an external ice-water bath
  8. stirringThe resulting suspension was stirred at ambient temperature for 14 hours
  9. filtrationThe solids were filtered off
  10. concentrationthe filtrate was concentrated under high vacuum
  11. customto obtain a colorless oil which

Sources & evidence

ORD record
ord-c701d4346a8140c7ac28475aaeae9203
Source dataset
uspto-grants-2008_05
Patent number
US07378432B2

Reaction notes

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