Water → HCID 86684977, compound

HRID 1505740Notes

Reaction equation

HRID 1505740 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[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]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2904984,6-Dichloroanthranilic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 86684977HCID 86684977, compoundYield 119.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-amino-4,6-dichlorobenzoic acid (10.0 g, 48.5 mmol) was dissolved in 50 mL of anhydrous THF in a 250 mL 2 neck round bottom flask. The solution was cooled in an ice-water bath. A solution of lithium aluminum hydride (LAH) (40 mL, 2.0 M) in THF 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. Water (5.1 mL) was added to the reaction mixture followed by 5.1 mL of 15% NaOH and then an additional 9.2 mL of water. The salts were filtered off and washed with THF. The filtrate was concentrated to give (2-amino-4,6-dichlorophenyl)methanol (11.1 g, wet) as a yellow solid, which was taken on to the next step without further purification.

Workup

  1. temperatureThe solution was cooled in an ice-water bath
  2. filtrationThe salts were filtered off
  3. washwashed with THF
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-700715d6cb284fdc9d30a703da2d0e6a
Source dataset
uspto-grants-2015_12
Patent number
US09217004B2

Reaction notes

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