Potassium Sodium Tartrate → (4-Amino-5-chloro-2-methoxyphenyl)methanol

HRID 1518627Notes

Reaction equation

HRID 1518627 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[C:16]([Cl:17])=[CH:15][C:11]([C:12](O)=[O:13])=[C:10]([O:18][CH3:19])[CH:9]=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[NH2:7][C:8]1[C:16]([Cl:17])=[CH:15][C:11]([CH2:12][OH:13])=[C:10]([O:18][CH3:19])[CH:9]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 55277042(4-Amino-5-chloro-2-methoxyphenyl)methanolYield 224.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (25.0 g, 116 mmol) in tetrahydrofuran (150 mL), 4-amino-5-chloro-2-methoxybenzoic acid (5 g, 28.0 mmol) was added in portions under ice-water cooling and the mixture was heated under reflux for 5 hours. Under ice-water cooling, a saturated aqueous solution of Rochelle salt was added to stop the reaction and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of Rochelle salt and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The solid obtained was washed with a mixed solvent of hexane-ethyl acetate (4:1), collected by filtration, and dried under reduced pressure to obtain 4-amino-5-chloro-2-methoxybenzyl alcohol (11.8 g)

Workup

  1. additionwas added in portions under ice-water cooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 5 hours
  4. customthe reaction
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of Rochelle salt
  7. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe solid obtained
  10. washwas washed with a mixed solvent of hexane-ethyl acetate (4:1)
  11. filtrationcollected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-71ced11e41d14b4c9f18461550fc1328
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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