Peracetic Acid → 2,6,6-Trimethyl-1-[1-hydroxy-3-butenyl]-1,2-epoxycyclohexane

HRID 1283359Notes

Reaction equation

HRID 1283359 reaction equation
C(OO)(=[O:3])C.C([O-])(=O)C.[Na+].[CH3:11][C:12]1[CH2:17][CH2:16][CH2:15][C:14]([CH3:19])([CH3:18])[C:13]=1[CH:20]([OH:24])[CH2:21][CH:22]=[CH2:23].C([O-])([O-])=O.[Na+].[Na+]>O.C(Cl)Cl>[CH3:11][C:12]12[O:3][C:13]1([CH:20]([OH:24])[CH2:21][CH:22]=[CH2:23])[C:14]([CH3:18])([CH3:19])[CH2:15][CH2:16][CH2:17]2

Participants

7

Reactant 4

HCID 6585Peracetic AcidHCID 10340Sodium CarbonateHCID 517045Sodium Acetate2×HCID 124203212,6,6-Trimethyl-1-(1-hydroxy-3-butenyl)-1-cyclohexene

Product 1

HCID 144665862,6,6-Trimethyl-1-[1-hydroxy-3-butenyl]-1,2-epoxycyclohexane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 40 % peracetic acid (105 g.) and anhydrous sodium acetate (3.0 g.) was added at 25° with stirring to a suspension of 2,6,6-trimethyl-1-[1-hydroxy-3-butenyl]-1-cyclohexene (97g.) and anhyd. sodium acetate (60 g.) in 175 ml. of CH2Cl2 (1.5 h.). Stirring was continued for one night and 500 ml. of water were then added to the reaction mixture. The organic layer was separated and, after the usual treatments, distilled to give 98 g. (83 %) of two diastereoisomers of the epoxy product. V.p.c. enabled the separation of the two isomers (Carbowax, 170°, 3 m)

Workup

  1. additionwas added at 25°
  2. waitwas continued for one night
  3. customThe organic layer was separated
  4. distillationafter the usual treatments, distilled
  5. customto give 98 g
  6. customthe separation of the two isomers (Carbowax, 170°, 3 m)

Sources & evidence

ORD record
ord-8aab5ecd46a64c0cafd13fd9fac7ba8f
Source dataset
uspto-grants-1976_08
Patent number
US03975310

Reaction notes

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