Acetic Acid → 4889-69-4

HRID 1448895Notes

Reaction equation

HRID 1448895 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=O)=[CH:4][CH:3]=1.C(O)(=O)C>[Zn].O>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]2[C:8]3[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10](=[O:12])[O:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 665642-(4'-Chlorobenzoyl)benzoic acid

Product 1

HCID 28846894889-69-4Yield 88%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

A five-liter, 3-neck flask fitted with a reflux condensor and drying tube, an air-driven stirring blade, and thermometer and temperature controller was charged with 2-(4'-chlorobenzoyl)benzoic acid (130.3 grams; 0.5 mol), zinc dust (490.3 g; 7.5 gram-atom), glacial acetic acid (2500 milliliters (ml)), and water (500 ml). The resulting mixture was heated, with stirring, under reflux temperatures (about 105° C.) for about 2 hours. The acetic acid solution was then decanted from the zinc and poured into 4 liters of cold water and the resulting white, fluffy needles were collected by filtration and dried at 60° C. at 10 mm of pressure for 14 hours. As a result of such operations, the desired 3-(4'-chlorophenyl)phthalide compound of Formula I was obtained in a yield of about 88%. Recrystallization from ethanol gave a purified product having an m.p. of 123.5°-124° C. as compared to a literature reference (Rec. Trav. Chim., 82, 801-805 (1963)) of 122°-125° C.

Workup

  1. customA five-liter, 3-neck flask fitted with a reflux condensor
  2. customdrying tube
  3. temperatureThe resulting mixture was heated
  4. customThe acetic acid solution was then decanted from the zinc
  5. additionpoured into 4 liters of cold water
  6. filtrationthe resulting white, fluffy needles were collected by filtration
  7. customdried at 60° C. at 10 mm of pressure for 14 hours
  8. customAs a result of such operations

Sources & evidence

ORD record
ord-5c84a0865d2443d08cb3e3a8d406d3e4
Source dataset
uspto-grants-1980_02
Patent number
US04188330

Reaction notes

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