Sodium sulfate decahydrate → (3-Benzyloxy-2-methyl-phenyl)-methanol

HRID 1964941Notes

Reaction equation

HRID 1964941 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:18])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([CH3:18])=[C:11]([CH2:12][OH:13])[CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 118068023-Benzyloxy-2-methyl-benzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 58087471(3-Benzyloxy-2-methyl-phenyl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzyloxy-2-methyl-benzoic acid (621, 3.0 g, 0.012 mol) in tetrahydrofuran (100 mL), lithium aluminum hydride (25 mL, 1M solution in tetrahydrofuran, 0.025 mol) was added dropwise at 0° C. for 5 minutes. The reaction mixture was then stirred at room temperature overnight under an atmosphere of nitrogen. After sodium sulfate decahydrate (20.0 g, 0.062 mol) was added, the reaction mixture was stirred at room temperature for 10 minutes. A white solid was collected by filtration. The solid compound was further washed with a mixture of hexane and dichloromethane (9:1) and dried under high-vacuum (622, 2.8 g, 91%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 10 minutes
  2. filtrationA white solid was collected by filtration
  3. washThe solid compound was further washed with a mixture of hexane and dichloromethane (9:1)
  4. customdried under high-vacuum (622, 2.8 g, 91%)

Sources & evidence

ORD record
ord-9bb44fcee10249df9b4b43caa2aab8b4
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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