Acetic Acid → HCID 12798025, compound

HRID 1106021Notes

Reaction equation

HRID 1106021 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:21]([CH3:23])[CH3:22])[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])=[CH:6][CH:5]=1)([O-])=O.C(O)(=O)C>[Fe].O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH:21]([CH3:23])[CH3:22])[C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 12798024HCID 12798024, compound

Product 1

HCID 12798025HCID 12798025, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Iron powder, 55 g, was added in portions to a stirred mixture of 94.6 g of 2-(4-nitrophenyl)-3-methylbutanoic acid, benzyl ester, 400 ml of acetic acid, and 100 ml of water, while the temperature was kept at 90°-95° by occasional application of an ice bath. After an additional 20 minutes at 90°-95°, the hot mixture was filtered, and the filtrate was diluted with water, precipitating an oil. The oil was extracted into butyl chloride, and the butyl chloride solution washed with water (3 times) and saturated sodium bicarbonate solution, dried (MgSO4) and evaporated to 85.7 g of orange oil, 2-(4-aminophenyl)-3-methylbutanoic acid, benzyl ester. Mass spectral analysis shows the expected molecular ion, m/e 283, of the product.

Workup

  1. customwas kept at 90°-95° by occasional application of an ice bath
  2. filtrationthe hot mixture was filtered
  3. additionthe filtrate was diluted with water
  4. customprecipitating an oil
  5. extractionThe oil was extracted into butyl chloride
  6. washthe butyl chloride solution washed with water (3 times) and saturated sodium bicarbonate solution
  7. dry with materialdried (MgSO4)
  8. customevaporated to 85.7 g of orange oil, 2-(4-aminophenyl)-3-methylbutanoic acid, benzyl ester

Sources & evidence

ORD record
ord-800ef6181d1746f4941a75cb5c3e2292
Source dataset
uspto-grants-1982_01
Patent number
US04311696

Reaction notes

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