Water → 1,2-Benzenedimethanol

HRID 472991

Reaction equation

HRID 472991 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-0b8e32ae7fa243aebe9cca9c6f902b45
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Linked notes

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