Water → 2-Amino-5-chloro-alpha-(2,4,6-trimethoxyphenyl)benzyl alcohol

HRID 1790Notes

Reaction equation

HRID 1790 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:3]=1[C:4]([C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([O:14][CH3:15])=[CH:8][C:7]=1[O:16][CH3:17])=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[NH2:1][C:2]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:3]=1[CH:4]([OH:5])[C:6]1[C:7]([O:16][CH3:17])=[CH:8][C:9]([O:14][CH3:15])=[CH:10][C:11]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 536989342-Amino-5-chloro-2',4',6'-trimethoxybenzophenone

Product 1

HCID 544145002-Amino-5-chloro-alpha-(2,4,6-trimethoxyphenyl)benzyl alcoholYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.0 g of 2-amino-5-chloro-2',4',6'-trimethoxybenzophenone in 50 ml of tetrahydrofuran, 0.43 g of lithium aluminum hydride was added, followed by stirring for 1 hour. After water was added, the solution was extracted with ethyl acetate and dried over anhydrous sodium sulfate, after which the solvent was removed and the residue was subjected to silica gel column chromatography to yield 2.9 g of a crystal.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. customafter which the solvent was removed

Sources & evidence

ORD record
ord-4ec01e77712840338ca5e710ce372103
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Reaction notes

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