Sodium Hydroxide → (4-Methyl-1,2-phenylene)dimethanol

HRID 1893529Notes

Reaction equation

HRID 1893529 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:9]=[C:10]2[C:15](=O)[O:14][C:12](=[O:13])[C:11]2=[CH:17][CH:18]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[CH3:7][C:8]1[CH:18]=[CH:17][C:11]([CH2:12][OH:13])=[C:10]([CH2:15][OH:14])[CH:9]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 880694-Methylphthalic anhydrideHCID 21226445Aluminium lithium hydride

Product 1

HCID 22243199(4-Methyl-1,2-phenylene)dimethanolYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To tetrahydrofuran (200 ml) was added lithium aluminum hydride (4.91 g, 129 mmol), and the mixture was stirred under ice-cooling. Then, a solution (100 ml) of 4-methylphthalic anhydride (10.4 g, 64.1 mmol) in tetrahydrofuran was added and the mixture was heated under reflux for 90 min. The reaction mixture was ice-cooled, and water (4.91 ml), 15% aqueous sodium hydroxide solution (4.91 ml), water (14.7 ml) and anhydrous magnesium sulfate were successively added with stirring. The insoluble material was filtered off through celite, and the solution was concentrated under reduced pressure to give the title compound (9.34 g, yield 96%) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 90 min
  4. temperaturecooled
  5. stirringwith stirring
  6. filtrationThe insoluble material was filtered off through celite
  7. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-55049119a58a4fdf92577b6f9c38ad64
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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