Water → (2-Amino-6-chlorophenyl)methanol

HRID 716590Notes

Reaction equation

HRID 716590 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4](O)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 750712-Amino-6-chlorobenzoic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 21925574(2-Amino-6-chlorophenyl)methanolYield 88.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-6-chlorobenzoic acid (25.0 g, 143 mmol) was dissolved in 120 mL of anhydrous THF in a 500 mL 2 neck round bottom flask. The solution was cooled in an ice-water bath. 215 mL of 1.0 M lithium aluminum hydride (LAH) THF solution was then added dropwise. After all of the LAH was added, the reaction mixture was allowed to warm up to room temperature and stirred at room temperature for overnight. ˜10 mL of water was added to the reaction mixture followed by 7 g 15% NaOH. An additional 20 g of water was added to the reaction mixture. Decant the organic THF phase and the solid was added with ethyl acetate. ˜200 mL and stirring and combined ethyl acetate organic portion and THF portion and added Na2SO4 drying agent. The mixture was filtered and evaporated. ˜20 g yellow solid was obtained without further purification for next step reaction.

Workup

  1. temperatureThe solution was cooled in an ice-water bath
  2. customDecant the organic THF phase
  3. additionthe solid was added with ethyl acetate
  4. stirring˜200 mL and stirring
  5. additionadded Na2SO4 drying agent
  6. filtrationThe mixture was filtered
  7. customevaporated

Sources & evidence

ORD record
ord-dfdb0103b7e84c6083fadd7273356a79
Source dataset
uspto-grants-2015_11
Patent number
US09190621B2

Reaction notes

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