Hydrochloric Acid → 4-Chloro-2-carboxyphenylacetonitrile

HRID 647418

Reaction equation

HRID 647418 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][O:7][C:8]2=[O:9])=[CH:4][CH:3]=1.[C-:12]#[N:13].[K+].Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:12]#[N:13])=[C:10]([C:8]([OH:7])=[O:9])[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 71741656-Chloro-3H-isobenzofuran-1-one

Product 1

HCID 126032044-Chloro-2-carboxyphenylacetonitrileYield 73.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 6-chlorophthalide (2.0 g) and potassium cyanide (2.0 g) was stirred at a temperature of 180° C. for a period of 4 hours. The solid was cooled, dissolved in water and the solution was acidified with concentrated hydrochloric acid. The dark brown solid was collected, washed with water and dried. The crude solid was dissolved in ethyl acetate, the solution was treated with charcoal, filtered, and the solvent was evaporated to give 4-chloro-2-carboxyphenylacetonitrile (1.70 g) as pale yellow crystals mp 120° C.

Workup

  1. temperatureThe solid was cooled
  2. customThe dark brown solid was collected
  3. washwashed with water
  4. customdried
  5. dissolutionThe crude solid was dissolved in ethyl acetate
  6. additionthe solution was treated with charcoal
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c2956ed37b054290b05212aa42a30c0c
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Linked notes

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