Hydrochloric Acid → 3-Phenoxybenzoyl chloride

HRID 1768516Notes

Reaction equation

HRID 1768516 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O.Cl.S(=O)=O>>[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([Cl:19])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 195393-Phenoxybenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 27603413-Phenoxybenzoyl chloride

Procedure

In a well ventilated hood, a mixture of m-phenoxy benzoic acid (200 g, 0.933 mole) (Aldrich) and thionyl chloride (105 mL, 1.44 moles) was placed in a one liter, round-bottomed flask. The flask was fitted with a magnetic stirring bar (or mechanical stirring bar for larger quantity preparation) and a reflux condenser with calcium chloride drying tube, which was attached to an exit tube, for evolved hydrogen chloride and sulfur dioxide, leading to a gas absorption trap. The mixture was heated on a heating mantle cautiously at first until a brownish-green solution was obtained (about 11/2 hours). The resulting solution was then heated gently for an additional 11/2 hours. The resulting brown solution was then cooled, and excessive thionyl chloride was distilled off at 40° C. To the resulting oil was added toluene (75 mL), and the solution was evaporated to remove a small amount of thionyl chloride. Addition and evaporation of toluene (75 mL) was repeated once more. The resulting acid chloride was then dissolved in 100 mL of tetrahydrofuran (THF dried over molecular sieves 3A), and ready to use freshly for reaction.

Workup

  1. customThe flask was fitted with a magnetic stirring bar
  2. custom(or mechanical stirring bar for larger quantity preparation) and a reflux condenser with calcium chloride drying tube
  3. customwhich was attached to an exit tube
  4. customleading to a gas absorption trap
  5. temperatureThe mixture was heated on a heating mantle cautiously at first until a brownish-green solution
  6. customwas obtained (about 11/2 hours)
  7. temperatureThe resulting solution was then heated gently for an additional 11/2 hours
  8. temperatureThe resulting brown solution was then cooled
  9. distillationexcessive thionyl chloride was distilled off at 40° C
  10. additionTo the resulting oil was added toluene (75 mL)
  11. customthe solution was evaporated
  12. customto remove a small amount of thionyl chloride
  13. additionAddition and evaporation of toluene (75 mL)
  14. dissolutionThe resulting acid chloride was then dissolved in 100 mL of tetrahydrofuran (THF dried over molecular sieves 3A)
  15. customready to use freshly for reaction

Sources & evidence

ORD record
ord-f6984926ab1d4080a1b5f9e6478c4d5c
Source dataset
uspto-grants-1995_01
Patent number
US05378636

Reaction notes

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