Ethyl Acetate → HCID 22272846, compound

HRID 1064829Notes

Reaction equation

HRID 1064829 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([OH:11])=[C:4]([N+:12]([O-])=O)[C:3]=1[CH3:15].C(OCC)(=O)C>C(O)(=O)C.[Zn]>[NH2:12][C:4]1[C:3]([CH3:15])=[C:2]([Cl:1])[CH:7]=[C:6]([CH:8]([CH3:9])[CH3:10])[C:5]=1[OH:11]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 22272691HCID 22272691, compound

Product 1

HCID 22272846HCID 22272846, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc (6.4 g, 98 mmol) was added little by little to a solution of the nitro compound (1.88 g, 8.18 mmol) in acetic acid (30 ml) with ice cooling. After stirring for 1 hour, the reaction solution was diluted by adding ethyl acetate thereto and the mixture was filtered off. The filtrate was neutralized with an aqueous solution of sodium carbonate and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over magnesium sulfate and the solvent was evaporated therefrom to provide 1.63 g (yield 99%) of 2-amino-4-chloro-6-isopropyl-3-methylphenol as pale yellow oil.

Workup

  1. additionthe reaction solution was diluted
  2. filtrationthe mixture was filtered off
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium chloride solution successively and dried over magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b0ac5ab53d9d4bc3867b4dab74a7f5a2
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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