Hydrochloric Acid → 4-(Aminomethyl)-2,6-dimethylphenol

HRID 2353594Notes

Reaction equation

HRID 2353594 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C:8]1[C:15]([CH3:16])=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=1[CH3:17].Cl>C(OCC)C.C1COCC1.O>[NH2:13][CH2:12][C:11]1[CH:10]=[C:9]([CH3:17])[C:8]([OH:7])=[C:15]([CH3:16])[CH:14]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 201763,5-Dimethyl-4-hydroxybenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 136687374-(Aminomethyl)-2,6-dimethylphenolYield 23.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of LiAlH4 (1.51 g, 39.8 mmol) in diethyl ether (40 mL) a solution of 4-hydroxy-3,5-dimethylbenzonitrile (4.89 g, 33.2 mmol) in diethyl ether (20 mL) and THF (10 mL) is added dropwise at rt. The mixture is stirred at rt for 22 h before it is cooled with an ice-bath and carefully treated with water (10 mL), acidified with 25% aq. HCl and diluted with water (30 mL). The mixture is extracted with diethyl ether. The etheral extract is discarded. The aqueous phase is basified to pH˜8 by adding solid NaHCO3, saturated with NaCl, and extracted with diethyl ether followed by EA. The combined organic extracts are dried over MgSO4 and evaporated to leave 4-aminomethyl-2,6-dimethyl-phenol (1.20 g) as a solid. LC-MS: tR=0.51 min, [M+1]+=152.19.

Workup

  1. additionis added dropwise at rt
  2. temperatureis cooled with an ice-bath
  3. extractionThe mixture is extracted with diethyl ether
  4. extractionThe etheral extract
  5. additionby adding solid NaHCO3
  6. extractionsaturated with NaCl, and extracted with diethyl ether
  7. dry with materialThe combined organic extracts are dried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-e6bdb5d882d54531a3d68b2123164792
Source dataset
uspto-grants-2010_07
Patent number
US07750040B2

Reaction notes

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