Hydrochloric Acid → 2-(3,4-Dihydroxyphenyl)acetonitrile

HRID 1721158Notes

Reaction equation

HRID 1721158 reaction equation
Cl.[C:2](#[N:14])[CH2:3][C:4]1[CH:13]=[CH:12][C:9]([O:10]C)=[C:6]([O:7]C)[CH:5]=1>N1C=CC=CC=1>[OH:10][C:9]1[C:6]([OH:7])=[CH:5][C:4]([CH2:3][C:2]#[N:14])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 667273,4-Dimethoxybenzeneacetonitrile

Product 1

HCID 109097272-(3,4-Dihydroxyphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
170 °C

Procedure

Hydrogen chloride gas is bubbled through a suspension of 2 moles (354 g) of homoveratronitrile in 161 ml of pyridine, with stirring and under a nitrogen atmosphere. As soon as the temperature reaches 115° C. and becomes stable, the bubbling is discontinued; the reaction medium is heated to 170° C. for 3 hours. During this period, hydrogen chloride is bubbled through for 5 to 10 minutes at approximately half-hourly intervals. When the reaction has ended, the reaction mixture is poured into a mixture of ice and water (1.2 kg).

Workup

  1. customreaches 115° C.
  2. waitDuring this period
  3. customhydrogen chloride is bubbled through for 5 to 10 minutes at approximately half-hourly intervals
  4. additionthe reaction mixture is poured into a mixture of ice and water (1.2 kg)

Sources & evidence

ORD record
ord-7723825a750d49ad896cfa4989730b3a
Source dataset
uspto-grants-1996_04
Patent number
US05508464

Reaction notes

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