Acetic Anhydride → 2-(3-Chloro-4-acetamidophenyl)acetic acid

HRID 2289100

Reaction equation

HRID 2289100 reaction equation
[C:1]([O:4]C(=O)C)(=O)[CH3:2].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1.[Cl:19][O-].[Ca+2].Cl[O-]>C(O)(=O)C.O.C(O)C>[Cl:19][C:14]1[CH:13]=[C:12]([CH2:15][C:16]([OH:18])=[O:17])[CH:11]=[CH:10][C:9]=1[NH:8][C:1](=[O:4])[CH3:2]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 145334-Aminophenylacetic acidHCID 24504Calcium hypochlorite

Product 1

HCID 187019472-(3-Chloro-4-acetamidophenyl)acetic acidYield 60.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

Acetic anhydride (152 mL, 1.6 moles) was added dropwise to a rapidly stirring mixture of 4-aminophenylacetic acid (195 grams, 1.3 moles) in acetic acid (600 mL) and water (250 mL) at room temperature. After a slight exotherm, the dark brown solution was stirred for one hour at room temperature. The solution was diluted with ethanol (500 mL) and water (250 mL), and a suspension of Calcium hypochlorite (340 grams, 2.3 moles) in water (1 L plus 500 mL rinse) was added portionwise. The temperature rose to 50° C. and the mixture was stirred for 16 hours at room temperature. The mixture was poured into ice-water (8 L) and extracted with ethyl acetate (3×2 L). The combined extracts were washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo to a small volume. Hexane was added and the resulting precipitate filtered, washed with hexane and dried to give the title compound(180 grams) as a brown solid

Workup

  1. stirringAfter a slight exotherm, the dark brown solution was stirred for one hour at room temperature
  2. additionwas added portionwise
  3. customrose to 50° C.
  4. stirringthe mixture was stirred for 16 hours at room temperature
  5. extractionextracted with ethyl acetate (3×2 L)
  6. washThe combined extracts were washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo to a small volume
  9. additionHexane was added
  10. filtrationthe resulting precipitate filtered
  11. washwashed with hexane
  12. customdried

Sources & evidence

ORD record
ord-d2adf5a56afd4068aaa9cd70d3ecaf0e
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Linked notes

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