2-Chlorobenzoic Acid → 2-Chlorobenzonitrile

HRID 361945Notes

Reaction equation

HRID 361945 reaction equation
[Cl-].[NH4+:2].[CH:3]1[CH:8]=[C:7]([C:9](O)=O)[C:6]([Cl:12])=[CH:5][CH:4]=1>>[CH:3]1[CH:8]=[C:7]([C:9]#[N:2])[C:6]([Cl:12])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 83742-Chlorobenzoic AcidHCID 25517Ammonium Chloride

Product 1

HCID 133912-ChlorobenzonitrileYield 880.8%

Conditions

Temperature
225 °C

Procedure

OCBTC (230 g, 1.0 mol), ammonium chloride (59 g, 1.10 eq), and OCBA (15.7 g) were added to a 500 mL reactor equipped with thermocouple, overhead stirrer, and reflux condenser. The reaction mixture was stirred, heated upto 225° C., and maintained at that temperature while the reaction was periodically followed by gas chromatography (GC). After a reaction time of about 8 h, OCBN (121.5 g, 88.4%) was obtained by distillation (melting point: 45°-46° C.).

Workup

  1. customequipped with thermocouple, overhead stirrer
  2. temperaturereflux condenser
  3. temperaturemaintained at that temperature while the reaction

Sources & evidence

ORD record
ord-d9940a7815c847f1bb7f83dba64cb78e
Source dataset
uspto-grants-1999_02
Patent number
US05866709

Reaction notes

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