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

HRID 1940021Notes

Reaction equation

HRID 1940021 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11](O)=[O:12])[C:5](=[CH:9][CH:10]=1)[C:6](O)=[O:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(OCC)(=O)C>O1CCCC1.CCCCCC>[OH:12][CH2:11][C:4]1[CH:3]=[C:2]([CH3:1])[CH:10]=[CH:9][C:5]=1[CH2:6][OH:7]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 203101,2-Benzenedicarboxylic acid, 4-methyl-HCID 21226445Aluminium lithium hydride

Product 1

HCID 22243199(4-Methyl-1,2-phenylene)dimethanolYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

4-Methylphthalic acid (1.40 g, 7.8 mmol) was dissolved in tetrahydrofuran (80 ml) under an argon atmosphere, and lithium aluminum hydride (742 mg, 19.5 mmol) was added, which was followed by reflux under heating for 4 hours. Water was added to the reaction mixture on an ice bath, and the mixture was extracted with ethyl acetate. The organic extract was washed successively with saturated aqueous potassium sodium tartrate solution, water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The obtained residue was separated and purified by silica gel column chromatography [developing solution: a mixed solution of ethyl acetate and hexane (volume ratio 2:3)] to give 759 mg of 3,4-dihydroxymethyltoluene (yield 64%).

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 4 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed successively with saturated aqueous potassium sodium tartrate solution, water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe obtained residue was separated
  10. custompurified by silica gel column chromatography [

Sources & evidence

ORD record
ord-74e71986e9a8417bb780bfebc6861dcd
Source dataset
uspto-grants-1997_12
Patent number
US05698580

Reaction notes

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