4-Formylbenzoic acid → 4-Formylbenzoyl chloride

HRID 13544

Reaction equation

HRID 13544 reaction equation
[Cl-].[Cl:2]C=[N+](C)C.[C:7]([C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1)(O)=[O:8]>C(Cl)Cl>[CH:14]([C:13]1[CH:16]=[CH:17][C:10]([C:7]([Cl:2])=[O:8])=[CH:11][CH:12]=1)=[O:15]

Participants

4

Reactant 2

HCID 120884-Formylbenzoic acidHCID 77311Chloro-N,N-dimethylformiminium chloride

Product 1

HCID 124246204-Formylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of (chloromethylene)dimethylammonium chloride (Vilsmeier Reagent; 37.7 g, 0.280 mol) in CH2Cl2 (300 mL) at 0° C. was treated with 4-carboxybenzaldehyde (40.0 g, 267 mmol) in one portion. The reaction mixture was stirred at 0° C. for 30 min, then at room temperature for 2 h. HPLC analysis of an aliquot of the reaction mixture quenched into MeOH indicated consumption of 4-carboxybenzaldehyde. The reaction mixture was filtered through a medium porosity glass frit. The filtrate, containing the title compound, was stored at 0° C., and used in the next step without further manipulation.

Workup

  1. waitat room temperature for 2 h
  2. customHPLC analysis of an aliquot of the reaction mixture quenched into MeOH
  3. customconsumption of 4-carboxybenzaldehyde
  4. filtrationThe reaction mixture was filtered through a medium porosity glass frit
  5. additionThe filtrate, containing the title compound
  6. customwas stored at 0° C.

Sources & evidence

ORD record
ord-a6cfdb8f7041403d96a62694f8d57739
Source dataset
uspto-grants-2010_06
Patent number
US07728129B2

Linked notes

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