Veratric Acid → Veratroyl chloride

HRID 647545Notes

Reaction equation

HRID 647545 reaction equation
S(Cl)([Cl:3])=O.[C:5]([OH:17])(=O)[C:6]1[CH:15]=[CH:14][C:11]([O:12][CH3:13])=[C:8]([O:9][CH3:10])[CH:7]=1>C1C=CC=CC=1.N1C=CC=CC=1>[C:5]([Cl:3])(=[O:17])[C:6]1[CH:15]=[CH:14][C:11]([O:12][CH3:13])=[C:8]([O:9][CH3:10])[CH:7]=1

Participants

5

Reactant 2

HCID 7121Veratric AcidHCID 24386Thionyl Chloride

Product 1

HCID 77070Veratroyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 241BenzeneSolvent

Procedure

In a 2-neck 100 ml-round bottom flask, 10.0 g (54.9 m mol) of veratric acid was dissolved in 50 ml of benzene, and after adding 2 to 3 drops of pyridine to the solution, 13 g (109 m mol) of thionyl chloride was dropped into the solution while stirring the solution at room temperature within 3 min. Then the content was heated to 70° to 80° C. on a water bath, and maintained at the temperature for 2 hours under a reflux condenser and agitation. Then, the solvent and excess thionyl chloride were evaporated off under a reduced pressure to obtain 11.0 g of veratroyl chloride as colourless powder in a yield of 100%.

Workup

  1. additionwas dropped into the solution
  2. temperatureThen the content was heated to 70° to 80° C. on a water bath
  3. temperaturemaintained at the temperature for 2 hours under a reflux condenser
  4. customThen, the solvent and excess thionyl chloride were evaporated off under a reduced pressure

Sources & evidence

ORD record
ord-8d27b4b4101f417b8a813033120aa681
Source dataset
uspto-grants-1983_10
Patent number
US04409240

Reaction notes

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