Peracetic Acid → 2-Oxiranepentanol, .gamma.,3,3-trimethyl-

HRID 2296389Notes

Reaction equation

HRID 2296389 reaction equation
C(OO)(=[O:3])C.[CH3:6][C:7](=[CH:9][CH2:10][CH2:11][CH:12]([CH2:14][CH2:15][OH:16])[CH3:13])[CH3:8].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:13][CH:12]([CH2:11][CH2:10][CH:9]1[O:3][C:7]1([CH3:8])[CH3:6])[CH2:14][CH2:15][OH:16]

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 8842CitronellolHCID 10340Sodium Carbonate

Product 1

HCID 984672-Oxiranepentanol, .gamma.,3,3-trimethyl-Yield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

210 g (1.1 M) of 40% peracetic acid were added dropwise within 1 h to a stirred suspension of 156 g (0.95 M; purity 95%) of citronellol kept at 0° and 53 g (0.5 M) of sodium carbonate in 200 ml of toluene. The reaction mixture was kept under stirring at 20° during 4 h then it was washed with water, a 5% solution of sodium sulfite and a 10% aqueous solution of NaHCO3. After drying over anhydrous sodium sulfate, evaporation of the solvent and distillation (70°-78°/20×102Pa), 139 g (yield 83%; purity 98%) of the desired epoxyde were obtained.

Workup

  1. customkept at 0°
  2. washit was washed with water
  3. dry with materialAfter drying over anhydrous sodium sulfate, evaporation of the solvent and distillation (70°-78°/20×102Pa), 139 g (yield 83%; purity 98%) of the desired epoxyde
  4. customwere obtained

Sources & evidence

ORD record
ord-278d720657b647e19f75eb900c939af2
Source dataset
uspto-grants-1984_01
Patent number
US04429139

Reaction notes

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