Hydrochloric Acid → 4-Chloro-3-(trifluoromethyl)benzaldehyde

HRID 1590375

Reaction equation

HRID 1590375 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5](N)=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].Cl.N([O-])=O.[Na+].[C:18]([O-])(=[O:20])C.[Na+].C=NO.Cl.C=NO.S([O-])([O-])=O.[Na+].[Na+].NC1C=CC=CC=1>O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([CH:18]=[O:20])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10]

Participants

10

Reactant 8

HCID 313Hydrochloric Acid2×HCID 6115AnilineHCID 6350NitroneHCID 24437Sodium SulfiteHCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 517045Sodium Acetate3×HCID 20257314Formaldehyde, oxime, hydrochloride (1:1)HCID 23668193Sodium Nitrite

Product 1

HCID 1186424-Chloro-3-(trifluoromethyl)benzaldehydeYield 8.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent5×

Procedure

To a suspension of 4-chloro-3-trifluoromethylaniline (ex Fluorochem) (15.9 g) in water (16 ml) was added concentrated hydrochloric acid (18 ml) Ice (30 g) was added and the mixture cooled to 0° and treated with sodium nitrite (5.6 g) in water (8 ml). After 15 minutes the mixture was made neutral to congo red with sodium acetate (8 g) in water (10 ml). A solution of formaldoxime, prepared from formaldoxime hydrochloride (ex Lancaster) (9.9 g) and sodium acetate (12 g) (ex BDH) in water (57 ml), at 10° was treated with cupric sulphate (2 g) (ex BDH) and sodium sulphite (0.34 g) followed by sodium acetate (55 g) in water (60 ml). The previously prepared mixture (from the aniline) was added dropwise at 10°-15°. After one hour at 15° hydrochloric acid (77 ml) was added and the mixture worked up in the usual manner. Purification by distillation (80°, 0.5 mmHg) gave 4-chloro-3-trifluoromethylbenzaldehyde (1.5 g).

Workup

  1. additionwas added
  2. temperaturethe mixture cooled to 0°
  3. customPurification
  4. distillationby distillation (80°, 0.5 mmHg)

Sources & evidence

ORD record
ord-32d3f09eb68347d3a7734a4a7956c177
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Linked notes

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