Peracetic Acid → HCID 6429141, compound

HRID 1658426Notes

Reaction equation

HRID 1658426 reaction equation
[CH3:1][C:2]([CH3:10])=[CH:3][CH2:4]/[CH:5]=[C:6](/[CH:8]=[CH2:9])\[CH3:7].C([O-])(=[O:13])C.[Na+].C(OO)(=O)C>C(Cl)Cl>[CH3:1][C:2]([CH3:10])=[CH:3][CH2:4][C@@H:5]1[O:13][C@@:6]1([CH:8]=[CH2:9])[CH3:7]

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 517045Sodium Acetate2×HCID 5281553Ocimene (E)

Product 1

HCID 6429141HCID 6429141, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 204 g. of trans-ocimene and 150 g. of sodium acetate in 750 ml. of methylene chloride was stirred for one hour at room temperature, then it was cooled to 0° C. within about 15 min. Then, the addition of a solution of 3 g. of sodium acetate in 315 g. of 42% peracetic acid was started dropwise at a rate adjusted so that the temperature rose to 20°-25°. Without removing the cooling device but by maintaining a suitable rate of addition, the temperature was kept constant until the addition of the peracetic acid was completed. Under these conditions, the addition took one hour. The mixture was stirred for an additional four hours period at room temperature then the solid was removed by filtration and rinsed with methylene chloride. The combined methylene chloride solutions were poured into ice-water, the resulting mixture was shaken vigorously and the organic layer was separated and washed with 125 ml. portions of the following solvents: water (1 fold), saturated Na2CO3 (2 fold), water (1 fold). After the usual drying and concentrating procedure, distillation of the residue gave 205 g. of trans-epoxyocimene (90% yield), b.p. 45°-47°/0.1 Torr. d420 = 0.9082; nD20 = 1.4802.

Workup

  1. additionThen, the addition of a solution of 3 g
  2. customrose to 20°-25°
  3. customWithout removing the cooling device
  4. temperatureby maintaining
  5. additiona suitable rate of addition
  6. additionthe temperature was kept constant until the addition of the peracetic acid
  7. additionUnder these conditions, the addition
  8. customthe solid was removed by filtration
  9. washrinsed with methylene chloride
  10. additionThe combined methylene chloride solutions were poured into ice-water
  11. stirringthe resulting mixture was shaken vigorously
  12. customthe organic layer was separated
  13. washwashed with 125 ml
  14. customAfter the usual drying
  15. concentrationconcentrating
  16. distillationprocedure, distillation of the residue
  17. customgave 205 g

Sources & evidence

ORD record
ord-f869f6f73ad44a80b5511bb3f89579b0
Source dataset
uspto-grants-1976_06
Patent number
US03963783

Reaction notes

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