3-Chlorobenzoic Acid → 4-Cyano-4'-glycidylbiphenyl

HRID 490032Notes

Reaction equation

HRID 490032 reaction equation
ClC1[CH:3]=[C:4](C=CC=1)[C:5]([OH:7])=O.C(O[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)C=C>C(Cl)Cl>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([C:18]2[CH:17]=[CH:16][C:15]([CH2:3][CH:4]3[O:7][CH2:5]3)=[CH:20][CH:19]=2)=[CH:26][CH:25]=1)#[N:28]

Participants

4

Reactant 2

HCID 4473-Chlorobenzoic AcidHCID 23419874-(4-Prop-2-enoxyphenyl)benzonitrile

Product 1

HCID 597905614-Cyano-4'-glycidylbiphenylYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 g of m-chlorobenzoic acid was added to a reaction mixture obtained by dissolving 19 g of 4-allyloxy-4′-cyanobiphenyl in 150 mL of methylene chloride as divided into several times, and the mixture was stirred at room temperature for 24 hours. Insoluble matters thus deposited were removed by filtration, and water was added thereto. After separating the mixture, the organic layer was washed with a saturated aqueous solution of sodium hydrosulfite and then dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain a residue, which was purified by silica gel column chromatography and then subjected to recrystallization from ethanol to obtain 13 g of 4-cyano-4′-glycidylbiphenyl.

Workup

  1. customobtained
  2. customInsoluble matters thus deposited were removed by filtration, and water
  3. additionwas added
  4. customAfter separating the mixture
  5. washthe organic layer was washed with a saturated aqueous solution of sodium hydrosulfite
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customto obtain a residue, which
  9. customwas purified by silica gel column chromatography
  10. customsubjected to recrystallization from ethanol

Sources & evidence

ORD record
ord-d38a5b3c246a4e6b9a13ec61341175c7
Source dataset
uspto-grants-2009_05
Patent number
US07527746B2

Reaction notes

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