Phosphorus oxide (P4O10) → HCID 15067977, compound

HRID 2165965Notes

Reaction equation

HRID 2165965 reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C[Si]([C:35]#[N:36])(C)C.[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[CH2:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([C:35]#[N:36])=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 14812Phosphorus oxide (P4O10)HCID 24287Tin tetrachlorideHCID 82115Trimethylsilyl cyanideHCID 1708644-Heptylbenzoyl chloride

Product 1

HCID 15067977HCID 15067977, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Heptylbenzoyl cyanide was synthesized according to the general procedure reported by G. A. Olah et al [supra]. Under dry conditions, 2.5518 g of 4-heptylbenzoyl chloride (99%, Aldrich) (10.69 mmol), 30 mL of methylene chloride, freshly distilled from phosphorus pentoxide under nitrogen, and 1.65 mL of trimethylsilyl cyanide (12 mmol) were added to a 100-mL round bottom flask. To this solution 0.27 mL of tin (IV) chloride (2.3 mmol) was added. The reaction mixture was stirred for 2 hr at room temperature. During the 2 hr, the color of the solution changed from a pale yellow to dark brown. After 2 hr of stirring, the reaction was quenched with 81 mL of ice-cold water and then extracted with two 81-mL portions of methylene chloride. The methylene chloride extracts were combined, washed with two 81-mL portions of ice-cold water, dried with MgSO4, and filtered. The methylene chloride was removed by rotary evaporation to yield 2.097 g of a dark brown oil. This oil was distilled at 106°-109.5° C. (0.2 mm) to yield 1.214 g (50%) of 4-heptylbenzoyl cyanide as a colorless oil that solidified on standing in the freezer: IR (CCl4) (partial) 2930, 2860, 2220, 1680, 1610 cm-1.

Workup

  1. customDuring the 2 hr
  2. stirringAfter 2 hr of stirring
  3. customthe reaction was quenched with 81 mL of ice-cold water
  4. extractionextracted with two 81-mL portions of methylene chloride
  5. washwashed with two 81-mL portions of ice-cold water
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customThe methylene chloride was removed by rotary evaporation

Sources & evidence

ORD record
ord-a0785ef8811748cd834d3b261d7fce93
Source dataset
uspto-grants-1990_07
Patent number
US04942247

Reaction notes

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