Hydrochloric Acid → 3-(4-n-Octylphenacyl)benzonitrile

HRID 1720155Notes

Reaction equation

HRID 1720155 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[CH2:19]([C:13]1[CH:14]=[CH:15][C:16]([C:10](=[O:12])[CH2:9][C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[C:1]#[N:2])=[CH:17][CH:18]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 16607OctylbenzeneHCID 15193972-(3-Cyanophenyl)acetic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 224204143-(4-n-Octylphenacyl)benzonitrileYield 31.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The acid chloride prepared from 3-cyanophenylacetic acid (5 g) as described in Example 18 is added at once to 1-phenyloctane (5.9 g, 0.03 moles) in methylene chloride (20 ml). Anhydrous aluminium chloride (4.96 g, 0.037 moles) is added in 1 portion and the resulting mixture heated under reflux for 2 hours. The reaction mixture is cooled and poured into a mixture of ice water (200 ml) and concentrated hydrochloric acid (20 ml). The mixture is extracted with ether (3×50 ml) and the combined extracts dried over magnesium sulfate, filtered, and evaporated to dryness. The residue is chromatographed on silica gel (hexane: ether; 70:30) to yield 3-(4-n-octylphenacyl)benzonitrile (3.12 g, m.p. 59°-64° C). This nitrile is heated under reflux in a mixture of concentrated hydrochloric acid (30 g) and acetic acid (30 g) for 48 hours. The reaction mixture is diluted with water (60 ml) and extracted with ether (3×50 ml). The combined ether extracts are washed with water (50 ml) then dried over magnesium sulfate, filtered, and evaporated to dryness. The residue is recrystallized from heptane and again from aqueous ethanol to provide 3-(4-octyl-phenacyl)benzoic acid (1.5 g), m.p. 103°-110° C.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture is cooled
  4. extractionThe mixture is extracted with ether (3×50 ml)
  5. dry with materialthe combined extracts dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue is chromatographed on silica gel (hexane: ether; 70:30)

Sources & evidence

ORD record
ord-091aa1b18b8e4fe486775f8af225a8e5
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

Loading…