Ethanol → Ethyl 2-(4-cyanophenyl)acetate

HRID 323974Notes

Reaction equation

HRID 323974 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-79897b9dccbf47cfb263db61a6fb6feb
Source dataset
uspto-grants-2001_04
Patent number
US06215001B1

Reaction notes

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