Water → 1,2-Benzenedimethanol

HRID 1503409Notes

Reaction equation

HRID 1503409 reaction equation
[C:1](O)(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4](O)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:2]1([CH2:1][OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 962WaterHCID 1017Phthalic AcidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 691531,2-BenzenedimethanolYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of phthalic acid (9 g, 0.05 mol) in anhydrous THF (200 mL) was added to LAH (7.6 g, 0.2 mol) in THF (250 mL) dropwise, and the mixture was refluxed for 18 hours. The mixture was cooled in ice bath and carefully added water dropwise, followed by 50% NaOH (150 mL), and then removed the ice bath added water slowly with stirring until the gray precipitate turns white. The mixture was filtrated and the filtrate was concentrated to give crude 1,2-phenylenedimethanol (7 g, 92%).

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. temperatureThe mixture was cooled in ice bath
  3. customremoved the ice bath
  4. additionadded water slowly
  5. filtrationThe mixture was filtrated
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a79c3c03810e4f7abdd94d9e9a65f2b8
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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