Dimethylformamide → 4-Formylbenzoyl chloride

HRID 1714107Notes

Reaction equation

HRID 1714107 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)(O)=[O:2].S(Cl)([Cl:14])=O.CN(C=O)C>C1(C)C=CC=CC=1>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([Cl:14])=[O:2])=[CH:5][CH:6]=1)=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 120884-Formylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 124246204-Formylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 4-carboxybenzaldehyde (30.0 g, 0.200 mol) in toluene (300 mL) was treated with thionyl chloride (28.6 g, 0.240 mol) and DMF (1.0 mL). The reaction mixture was heated at 100° C. for 2 h, during which time the solids dissolved to yield a pale yellow colored solution. The reaction mixture was cooled to 0° C. to yield a solution of the title compound in toluene, which was used without further manipulation.

Workup

  1. dissolutiondissolved
  2. customto yield a pale yellow colored solution
  3. temperatureThe reaction mixture was cooled to 0° C.

Sources & evidence

ORD record
ord-8565ee379d35483a8124f75a20331662
Source dataset
uspto-grants-2010_09
Patent number
US07795426B2

Reaction notes

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