Sodium sulfate decahydrate → (2-(Aminomethyl)phenyl)methanol

HRID 1939946Notes

Reaction equation

HRID 1939946 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])#[N:8].O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[OH:12][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=1[CH2:7][NH2:8]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 1012092-CyanobenzaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 11275036(2-(Aminomethyl)phenyl)methanolYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminium hydride (17.4 g, 458 mmol) was suspended in dried tetrahydrofuran (300 ml), followed by stirring under ice-cooling in an argon atmosphere. A solution of 2-cyanobenzaldehyde (20.0 g, 153 mmol) dissolved in dried tetrahydrofuran (100 ml) was dropwise and portionwise added thereto and the reaction solution was stirred for 3 hours under heating at reflux. After the reaction, the solution was ice-cooled and sodium sulfate 10 hydrate was portionwise added thereto until foaming and fever ceased. The reaction solution was filtered and the filtrate was concentrated to give the title compound (20.9 g, quantitative) as oily substances. This compound was used in the subsequent reaction without further purification.

Workup

  1. temperaturecooling in an argon atmosphere
  2. additionportionwise added
  3. stirringthe reaction solution was stirred for 3 hours
  4. temperatureunder heating
  5. temperatureat reflux
  6. customAfter the reaction
  7. temperaturecooled
  8. filtrationThe reaction solution was filtered
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3beecae5e04e413fac3b559da0f6b3ca
Source dataset
uspto-grants-1997_12
Patent number
US05698560

Reaction notes

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