Ethanol → Ethyl 2-(4-cyanophenyl)acetate

HRID 1956871Notes

Reaction equation

HRID 1956871 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)#[N:2].S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:18][CH3:19])=[O:11])=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 795874-Cyanophenylacetic acid

Product 1

HCID 279718Ethyl 2-(4-cyanophenyl)acetate

Procedure

A suspension of 4-cyanophenylacetic acid (31.2 g, prepared as described in J.C.S. 744, (1941)), concentrated sulphuric acid (5 ml) and absolute ethanol (300 ml) was boiled under reflux with stirring for 48 hours. The solvent was removed under reduced pressure and dilute aqueous sodium hydroxide solution was added to neutralise the sulphuric acid. Dichloromethane was added. The mixture was filtered and extracted with further dichloromethane. The organic extracts were dried and evaporated to give ethyl 4-cyanophenylacetate, m.p. 94°-95° C.

Workup

  1. temperatureunder reflux
  2. customThe solvent was removed under reduced pressure and dilute aqueous sodium hydroxide solution
  3. additionwas added
  4. additionDichloromethane was added
  5. filtrationThe mixture was filtered
  6. extractionextracted with further dichloromethane
  7. customThe organic extracts were dried
  8. customevaporated

Sources & evidence

ORD record
ord-6c546c7fd6b64f5780142881ad5efc32
Source dataset
uspto-grants-1998_07
Patent number
US05780642

Reaction notes

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