Dimethyl Sulfoxide → HCID 53804914, compound

HRID 440534Notes

Reaction equation

HRID 440534 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[CH2:11][C:12]([CH3:16])(C)[CH2:13]I.[OH-].[K+].[CH3:19]S(C)=O>>[CH3:11][C:12]1([CH3:16])[CH2:13][CH2:19][C:7]1([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]#[N:9]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8794PhenylacetonitrileHCID 14797Potassium HydroxideHCID 3134881,3-diiodo-2,2-dimethylpropane

Product 1

HCID 53804914HCID 53804914, compound

Procedure

A mixture of phenylacetonitrile (47.4 g) and 1,3-diiodo-2,2-dimethylpropane (131.2 g) was added dropwise over 2 hours at 25° C. to a stirred solution of powdered potassium hydroxide (90.7 g) in dry dimethylsulphoxide (600 ml) under a nitrogen atmosphere. The mixture was stirred overnight then poured onto water and extracted with ether (1000 ml). The extracts were decolourised with charcoal, filtered and concentrated in vacuo to yield an orange-brown oil which was distilled under vacuum to give 2,2-dimethyl-1-phenylcyclobutane carbonitrile, (b.p. 101°-106° C./0.6mbar) as a pale yellow oil.

Workup

  1. additionthen poured onto water
  2. extractionextracted with ether (1000 ml)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto yield an orange-brown oil which
  6. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-0dee793e50754cd9ac2e9853cd3e5b2b
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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