3-Chlorobenzoic Acid → HCID 21963701, compound

HRID 461401Notes

Reaction equation

HRID 461401 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:18])C=1.ClC1C=C(C=CC=1)C(O)=O>C(Cl)(Cl)Cl>[CH2:1]([C:4]12[O:18][CH:5]1[CH:6]=[CH:7][CH:8]=[CH:9]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 9309AllylbenzeneHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 21963701HCID 21963701, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

21.6 g of allylbenzene was dissolved in 200 ml of chloroform and to the mixture was added dropwise 41.4 g of m-chloroperbenzoic acid dissolved in 1l of chloroform at 0° - 5° C. The resulting mixture was reacted with slow stirring for 55 hours while maintaining the temperature at 0° - 5° C. After the completion of the reaction, m-chlorobenzoic acid crystals were filtered off and the filtrate was washed twice with 5% sodium hydroxide solution and then water. After dried over anhydrous sodium sulfate, the solvent was evaporated to obtain the residue. This was distilled under reduced pressure to give 16.9 g (yield 70.5%) of allylbenzene oxide as colourless oil having a boiling point of 60° C/2 mmHg.

Workup

  1. customThe resulting mixture was reacted
  2. temperaturewhile maintaining the temperature at 0° - 5° C
  3. filtrationwere filtered off
  4. washthe filtrate was washed twice with 5% sodium hydroxide solution
  5. dry with materialAfter dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customto obtain the residue
  8. distillationThis was distilled under reduced pressure

Sources & evidence

ORD record
ord-6faebba765e943b2b678bb717b5c234f
Source dataset
uspto-grants-1977_12
Patent number
US04062862

Reaction notes

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