Acetic Acid → 3-(4-n-Heptylphenacyl)benzoic acid

HRID 1720154Notes

Reaction equation

HRID 1720154 reaction equation
[CH2:1]([C:8]1[CH:24]=[CH:23][C:11]([C:12](=[O:22])[CH2:13][C:14]2[CH:15]=C([CH:19]=[CH:20][CH:21]=2)C#N)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:25]([OH:28])(=[O:27])[CH3:26]>S(=O)(=O)(O)O.O>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([C:12](=[O:22])[CH2:13][C:14]2[CH:15]=[C:26]([CH:19]=[CH:20][CH:21]=2)[C:25]([OH:28])=[O:27])=[CH:23][CH:24]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 224204113-(4-n-Heptylphenacyl)benzonitrile

Product 1

HCID 152955733-(4-n-Heptylphenacyl)benzoic acidYield 1.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 3-cyanophenylacetic acid (13 g, 0.08 mole) and thionyl chloride (100 ml) is heated under reflux for 90 minutes. The excess thionyl chloride is removed by evaporation under reduced pressure. The residue is dissolved in methylene chloride (20 ml) and the resulting solution added to aluminum chloride (16.2 g, 0.12 mole) in methylene chloride (200 ml) with vigorous stirring. A solution of 1-phenylheptane (14.3 g, 0.12 mole) in methylene chloride (50 ml) is then added over 20 minutes. The reaction mixture is heated under reflux (1 hour) and then poured into ice water (1 liter) with vigorous stirring. The mixture is extracted twice with ether (600 ml and 100 ml). The extracts are combined, dried over magnesium sulfate and evaporated under reduced pressure. The residue is chromatographed on silica gel (hexane/ether) to give 3-(4-n-heptylphenacyl)benzonitrile (7.6 g) as a White crystalline solid, m.p. 68° C. Then, 3-(4-n-heptylphenacyl)benzonitrile (1.5 g, 4.7 mole) is heated under reflux (1 hour) in a mixture of 75% aqueous sulfuric acid (12 g) and acetic acid (12 g). The reaction mixture is diluted with water (100 ml) and extracted with ether (2×75 ml). The ether extract is dried over magnesium sulfate, filtered and evaporated under reduced pressure. The resulting yellow solid is chromatographed on silica gel (hexane:ether:acetic acid; 60:40:1) and recrystallized from heptane to give 3-(4-n-heptylphenacyl)benzoic acid (1 g) as a pale yellow crystalline solid, 128°-133°C.

Workup

  1. temperatureunder reflux (1 hour)
  2. extractionextracted with ether (2×75 ml)
  3. extractionThe ether extract
  4. dry with materialis dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe resulting yellow solid is chromatographed on silica gel (hexane:ether:acetic acid; 60:40:1)
  8. customrecrystallized from heptane

Sources & evidence

ORD record
ord-9825d48bde2f4a1bba1adc37464aeeb2
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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