3-Chlorobenzoic Acid → Safrole oxide

HRID 461403

Reaction equation

HRID 461403 reaction equation
[O:1]1[C:12]2[C:4](=[CH:5][C:6](=[CH:10][CH:11]=2)[CH2:7][CH:8]=[CH2:9])[O:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:21])C=1.ClC1C=C(C=CC=1)C(O)=O>C(Cl)(Cl)Cl>[O:1]1[C:12]2[C:4](=[CH:5][C:6](=[CH:10][CH:11]=2)[CH2:7][CH:8]2[O:21][CH2:9]2)[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 5144SafroleHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 101123Safrole oxideYield 39.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

16.2 g of safrole was dissolved in 100 ml of chloroform and to the mixture was added dropwise 20.7 g of m-chloroperbenzoic acid dissolved in 500 ml of chloroform at 0°-5° C. The resulting mixture was allowed to stand 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 and the filtrate was washed twice with 5% sodium hydroxide solution, and then with water. After drying over anhydrous sodium sulfate, the solvent was evaporated to obtain the residue. This was distilled under reduced pressure to give 7.0 g (yield 39.3%) of safrole oxide as colourless oily substance having a boiling point of 108° - 110° C/3 mmHg.

Workup

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

Sources & evidence

ORD record
ord-2b54d2f2b524405692cee26bdb19a316
Source dataset
uspto-grants-1977_12
Patent number
US04062862

Linked notes

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