Benzoic Acid → 4-Vinylbenzoyl chloride

HRID 1607950Notes

Reaction equation

HRID 1607950 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1)=[CH2:2].S(Cl)([Cl:14])=O.C(O)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl.[N+](C1C=CC=CC=1)([O-])=O>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:14])=[O:8])=[CH:5][CH:4]=1)=[CH2:2]

Participants

6

Reactant 3

HCID 243Benzoic AcidHCID 140984-Vinylbenzoic acid3×HCID 24386Thionyl Chloride2×

Product 1

HCID 110520284-Vinylbenzoyl chlorideYield 91%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7416NitrobenzeneSolvent

Conditions

Temperature
50 °C

Procedure

4-vinyl benzoyl chloride was synthesized from 4-vinyl benzoic acid (obtained from Trans World Chemicals). The 4-vinyl benzoic acid was dissolved in chloroform with a small (0.16 mole/mole 4-vinyl benzoic acid) amount of nitrobenzene added as an inhibitor to prevent cross-linking. A large excess of thionyl chloride (six times the moles of benzoic acid) was added dropwise while stirring and gently heating to 50° C. Once the thionyl chloride was completely added, and the solution was at a temperature of 50° C., it was allowed to stir for one hour. The solution was then distilled (rotary evaporator) to remove the bulk of the chloroform and unreacted thionyl chloride. The impure 4-vinylbenzoyl chloride was then vacuum distilled to further purify it. At <1 mm mercury the 4-vinylbenzoyl chloride distills at around 70° C. The composition of the product was checked by NMR and was confirmed to be 4-vinylbenzoyl chloride. The yield was 91%.

Workup

  1. additionadded as an inhibitor
  2. customwas at a temperature of 50° C., it
  3. stirringto stir for one hour
  4. distillationThe solution was then distilled
  5. custom(rotary evaporator)
  6. customto remove the bulk of the chloroform and unreacted thionyl chloride
  7. distillationvacuum distilled
  8. customto further purify it
  9. distillationAt <1 mm mercury the 4-vinylbenzoyl chloride distills at around 70° C

Sources & evidence

ORD record
ord-d36dd764261d4837b7a95cb6cde136f8
Source dataset
uspto-grants-1989_09
Patent number
US04868241

Reaction notes

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