Ethanol → Ethyl 2-(4-cyanophenyl)acetate

HRID 378635Notes

Reaction equation

HRID 378635 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-9729bb75212645678bba8277419c5356
Source dataset
uspto-grants-2000_02
Patent number
US06031109

Reaction notes

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