Formic Acid → 4-Chlorobenzonitrile

HRID 1493798Notes

Reaction equation

HRID 1493798 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C([O-])=O.[Na+].Cl.[NH2:15]O.C(O)=O>O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 77264-ChlorobenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium Formate

Product 1

HCID 121634-ChlorobenzonitrileYield 86.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

4-chlorobenzaldehyde (50 g; 0.36 mol), sodium formate (48.4 g; 0.71 mol), and hydroxylamine hydrochloride (24.7 g; 0.36 mol) were added to 400 ml formic acid (98 wt. %). The reaction mixture was refluxed for 1 hour at 130° C., cooled to room temperature and poured into 1 liter cold water to produce a white precipitate, which was filtered and air-dried to yield 43 g 4-chlorobenzonitrile (m.p.=91°-92° C.). The yield for this step in the reaction sequence was about 88%.

Workup

  1. temperaturecooled to room temperature
  2. customto produce a white precipitate, which
  3. filtrationwas filtered
  4. customair-dried

Sources & evidence

ORD record
ord-dd5149695ca14e71a7b2daf95438aaf3
Source dataset
uspto-grants-1991_06
Patent number
US05024673

Reaction notes

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