Benzene → HCID 54324094, compound

HRID 1655110Notes

Reaction equation

HRID 1655110 reaction equation
[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:14][S:15]([CH2:18][C:19]#[N:20])(=[O:17])=[O:16].N1C=CC=CC=1.C1C=CC=CC=1>N1CCCCC1.O>[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[C:18]([C:19]#[N:20])[S:15]([CH3:14])(=[O:17])=[O:16])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 241BenzeneHCID 1049PyridineHCID 75283(Methylsulfonyl)acetonitrileHCID 798134-Butoxybenzaldehyde

Product 1

HCID 54324094HCID 54324094, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 962WaterSolvent

Procedure

A mixture of 20.0 g (0.112 mol) of 4-butoxybenzaldehyde, 13.6 g (0.114 mol) of methylsulfonylacetonitrile, 8.9 g (0.11 mol) of pyridine, 4 drops of piperidine, and 100 mL of benzene were heated at reflux for 18 hr, with continuous azeotropic separation of the water evolved. Approximately half of the benzene was then distilled, and 50 mL of heptane was added. Upon cooling to room temperature, a white precipitate was formed, which was collected and recrystallized twice from toluene to afford 15.3 g (49%) of (5). A sample of (5) that was sublimed in vacuo melted at 96.5°-7° C.

Workup

  1. temperaturewere heated
  2. distillationApproximately half of the benzene was then distilled
  3. addition50 mL of heptane was added
  4. customa white precipitate was formed
  5. customwhich was collected
  6. customrecrystallized twice from toluene

Sources & evidence

ORD record
ord-033b60020ff74f018c5586b12033b8c9
Source dataset
uspto-grants-1995_04
Patent number
US05410630

Reaction notes

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