Acetonitrile → 3-Phenoxybenzoylacetonitrile

HRID 465272Notes

Reaction equation

HRID 465272 reaction equation
C[O-].[Na+].CO[C:6](=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1.[C:21](#[N:23])[CH3:22]>>[O:13]([C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:6]([CH2:22][C:21]#[N:23])=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 198261Methyl 3-phenoxybenzoateHCID 10942334Sodium Methoxide

Product 1

HCID 198735383-PhenoxybenzoylacetonitrileYield 65%

Procedure

A solution of sodium methoxide (from 1.2 g sodium in 25 ml methanol) was added dropwise over 2 hours to a refluxing solution of methyl-3-phenoxybenzoate (11 g) in acetonitrile (100 ml) under a nitrogen atmosphere while distilling off methanol and excess acetonitrile. After complete removal of methanol the reaction mixture was poured onto ice-water (200 g) and acidified with 50% HCl. The solid was filtered off and dried to give the title compound (7.5 g, 65%) as a white solid of m.p. 95°-96° C.

Workup

  1. distillationwhile distilling off methanol and excess acetonitrile
  2. customAfter complete removal of methanol the reaction mixture
  3. additionwas poured onto ice-water (200 g)
  4. filtrationThe solid was filtered off
  5. customdried

Sources & evidence

ORD record
ord-c8d0c49d523a447ab662d3235cb90973
Source dataset
uspto-grants-1992_10
Patent number
US05152825

Reaction notes

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