Potassium Hydroxide → 2-Amino-5-methylbenzyl alcohol

HRID 1612865Notes

Reaction equation

HRID 1612865 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:9]=1[C:10](O)=[O:11].[OH-].[K+]>C1COCC1.O>[OH:11][CH2:10][C:9]1[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:8]=1[NH2:7]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 762552-Amino-5-methylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 5764502-Amino-5-methylbenzyl alcohol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.3 l of a 1.3 molar lithium aluminium hydride solution in THF are added dropwise under reflux to a solution of 100 g (0.66 mol) of 2-amino-5-methylbenzoic acid in 400 ml of anhydrous tetrahydrofuran. After addition is complete, the mixture is additionally heated under reflux for 1.5 h and hydrolysed at this temperature using a solution of 36 g of potassium hydroxide in 145 ml of water. After boiling under reflux for a further 15 min, the hydroxide precipitate is filtered off while hot, the precipitate is washed with ethyl acetate, the organic solution is concentrated in vacuo, the residue is dissolved in ethyl acetate and the solution is washed with dilute sodium hydroxide solution and water. After drying with sodium sulphate and concentrating the solution, the residue is recrystallised from ethyl acetate.

Workup

  1. additionAfter addition
  2. temperaturethe mixture is additionally heated
  3. temperatureunder reflux for 1.5 h and hydrolysed at this temperature
  4. temperatureunder reflux for a further 15 min
  5. filtrationthe hydroxide precipitate is filtered off while hot, the precipitate
  6. washis washed with ethyl acetate
  7. concentrationthe organic solution is concentrated in vacuo
  8. dissolutionthe residue is dissolved in ethyl acetate
  9. washthe solution is washed with dilute sodium hydroxide solution and water
  10. dry with materialAfter drying with sodium sulphate
  11. concentrationconcentrating the solution
  12. customthe residue is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-33e6d22d592d400bacb4c8714ca9802a
Source dataset
uspto-grants-1993_03
Patent number
US05190971

Reaction notes

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