Benzene → 4-[2-(Bromomethyl)-1,3-dioxolan-2-yl]benzonitrile

HRID 1679129Notes

Reaction equation

HRID 1679129 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=[O:4].[CH2:13]([OH:17])[CH2:14]CC.CC1C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C(O)CO>[Br:1][CH2:2][C:3]1([C:5]2[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=2)[O:17][CH2:13][CH2:14][O:4]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 986544-(Bromoacetyl)benzonitrile

Product 1

HCID 27969044-[2-(Bromomethyl)-1,3-dioxolan-2-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a stirred solution of 112 parts of 4-(2-bromoacetyl)benzonitrile in 320 parts of butanol are added 5 parts of 4-methylbenzenesulfonic acid and 360 parts of benzene. Then there are added dropwise 46.5 parts of 1,2-ethanediol. Upon completion, stirring is continued for 4 hours at reflux. The reaction mixture is evaporated. The oily residue is crystallized from 2,2'-oxybispropane. The product is filtered off and recrystallized from methanol, yielding 95.12 parts of 4-[2-(bromomethyl)-1,3-dioxolan-2-yl]-benzonitrile; mp. 92.4° C..

Workup

  1. temperatureat reflux
  2. customThe reaction mixture is evaporated
  3. customThe oily residue is crystallized from 2,2'-oxybispropane
  4. filtrationThe product is filtered off
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5e1c154d45ce413fa7fa1bd077043076
Source dataset
uspto-grants-1978_03
Patent number
US04079062

Reaction notes

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