Tetrahydrofuran → (2-Methyl-1,4-phenylene)dimethanol

HRID 1682094Notes

Reaction equation

HRID 1682094 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH3:12][C:13]1[CH:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][C:14]=1[CH:15]=[O:16].[OH-].[Na+]>O>[OH:16][CH2:15][C:14]1[CH:17]=[CH:18][C:19]([CH2:21][OH:22])=[CH:20][C:13]=1[CH3:12]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 590599HCID 590599, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19065812(2-Methyl-1,4-phenylene)dimethanolYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 200 ml round-bottomed flask was charged with 1 g (25 mmol) of lithium aluminum hydride, and under an argon atmosphere, 50 ml of anhydrous tetrahydrofuran was added. While the resultant mixture was stirred, 50 ml of an anhydrous tetrahydrofuran solution of 2.8 g (19 mmol) of 2-methylterephthalaldehyde was added through a dropping funnel over 20 minutes. The resultant mixture was heat-refluxed for 2 hours, and while the reaction mixture was hot, 1 ml of water, 1 ml of a 50% sodium hydroxide aqueous solution and 3 ml of water were consecutively added in this order. A white precipitate formed was separated by filtering, and the tetrahydrofuran solution was dried over magnesium sulfate, followed by distilling the solvent off with a rotary evaporator and drying under reduced pressure, whereby 2.7 g (18 mmol) of 2,5-bis(hydroxymethyl)toluene was obtained (yield 95%).

Workup

  1. customA white precipitate formed
  2. customwas separated
  3. filtrationby filtering
  4. dry with materialthe tetrahydrofuran solution was dried over magnesium sulfate
  5. distillationby distilling the solvent
  6. customoff with a rotary evaporator
  7. customdrying under reduced pressure

Sources & evidence

ORD record
ord-2c2aac9fb42a429182bc6bf0b81c75d1
Source dataset
uspto-grants-1992_12
Patent number
US05175280

Reaction notes

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