Safrole → Safrole oxide

HRID 2057693Notes

Reaction equation

HRID 2057693 reaction equation
[CH2:1]([C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)[CH:2]=[CH2:3].CCC(OO)=[O:16]>C1C=CC=CC=1>[O:16]1[CH2:3][CH:2]1[CH2:1][C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 5144SafroleHCID 65136Perpropionic acid

Product 1

HCID 101123Safrole oxide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

305 g of 5-(2-propenyl)-1,3-benzodioxole were reacted with 105 g of a 21.52% strength solution of perpropionic aicd in benzene at 32° C. as described in Example 1. After a reaction time of 2.5 hours, the peracid conversion was 98%. 5-(Oxiranylmethyl)-1,3-benzodioxole was formed with a selectivity of 85%. For working up, the reaction mixture was introduced into a distillation unit operating with a thin film evaporator and was separated into a top product, which contained benzene, propionic acid and unreacted 5-(2-propenyl)-1,3-benzodioxole, and into a bottom product, which consisted essentially of 5-(oxiranylmethyl)-1,3-benzodioxole. After redistillation of this bottom product, 37.0 g of 5-(oxiranylmethyl)-1,3-benzodioxole were obtained in a purity of 99.9%.

Workup

  1. customAfter a reaction time of 2.5 hours

Sources & evidence

ORD record
ord-25c79ac76a054549bab77e711e93b120
Source dataset
uspto-grants-1980_07
Patent number
US04212809

Reaction notes

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