Salicylic Acid → Salicyloyl chloride

HRID 1359154Notes

Reaction equation

HRID 1359154 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>N1C=CC=CC=1.C1(C)C=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 Chloride2×

Product 1

HCID 74041Salicyloyl chloride

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 1140TolueneSolvent2×

Procedure

Into a clean, dry three necked round bottomed flask were charged one equivalent of salicylic acid, 50 mls is of anhydrous toluene and a few drops of pyridine catalyst. The flask was equipped with a stir bar, thermometer and an addition funnel. Into the addition funnel was charged one equivalent of thionyl chloride in a few mls of toluene. The contents of the reaction flask were heated to 40° C. under a nitrogen blanket before the thionyl chloride solution was added slowly. Once the addition was complete, the reaction proceeded at 40-45° C. for several hours or until the reaction mixture was homogeneous. Upon completion of the reaction, any unreacted thionyl chloride was removed under vacuum.

Workup

  1. customInto a clean, dry three necked round bottomed flask
  2. customThe flask was equipped with a stir bar
  3. additionwas added slowly
  4. additionOnce the addition
  5. waitthe reaction proceeded at 40-45° C. for several hours or until the reaction mixture
  6. customUpon completion of the reaction
  7. customany unreacted thionyl chloride was removed under vacuum

Sources & evidence

ORD record
ord-47ba55cb89484757af31382dc8122ad8
Source dataset
uspto-grants-2003_07
Patent number
US06599936B1

Reaction notes

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