Sodium sulfate decahydrate → (3-(Phenylamino)phenyl)methanol

HRID 2422268

Reaction equation

HRID 2422268 reaction equation
[NH:1]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11](OC)=[O:12])[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.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH:1]([C:8]1[CH:9]=[C:10]([CH2:11][OH:12])[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 614856Methyl 3-(phenylamino)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12882229(3-(Phenylamino)phenyl)methanolYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution (22 mL) of methyl 3-anilinobenzoate (2.13 g, 9.37 mmol) in tetrahydrofuran was added lithium aluminum hydride (0.36 g, 9.37 mmol) with stirring at 0° C., and the mixture was stirred at the same temperature for 2 hrs. Sodium sulfate 10 hydrate (9.1 g, 28.1 mmol) was gradually added to the reaction mixture and the mixture was stirred at room temperature for 5 hrs. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1) to give the title compound (1.12 g, yield 60%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hrs
  2. stirringthe mixture was stirred at room temperature for 5 hrs
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1)

Sources & evidence

ORD record
ord-356c1740416a43bcb927fd00461a1055
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Linked notes

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