Salicylic Acid → Salicyloyl chloride

HRID 1620894Notes

Reaction equation

HRID 1620894 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].S(Cl)([Cl:13])=O>CCCCCC.N1C=CC=CC=1>[C:1]([Cl:13])(=[O:10])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

5

Reactant 2

HCID 338Salicylic AcidHCID 24386Thionyl Chloride

Product 1

HCID 74041Salicyloyl chloride

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 8058HexaneSolvent

Procedure

Salicylic acid (5.0 g, 36.2 mmol) was suspended in dry hexane (40 ml) and thionyl chloride (4.52 g, 38 mmol) was added under nitrogen atmosphere followed by one drop of pyridine. The mixture was refluxed for two hours while stirring. The clear yellow solution was cooled and concentrated in vacuum, giving a dense oil to be used in the next step.

Workup

  1. temperatureThe mixture was refluxed for two hours
  2. temperatureThe clear yellow solution was cooled
  3. concentrationconcentrated in vacuum
  4. customgiving a dense oil

Sources & evidence

ORD record
ord-26f14ecbbf42487ba7dd5936f4012a93
Source dataset
uspto-grants-2014_07
Patent number
US08772503B2

Reaction notes

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