m-Chloroperbenzoic acid → HCID 13021464, compound

HRID 1680946Notes

Reaction equation

HRID 1680946 reaction equation
[Br:1][CH2:2][C:3](=[O:14])[CH2:4][CH2:5][CH:6]=[C:7]([CH3:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)Cl>[Br:1][CH2:2][C:3](=[O:14])[CH2:4][CH2:5][CH:6]1[O:23][C:7]1([CH3:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54047845HCID 54047845, compound

Product 1

HCID 13021464HCID 13021464, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1-Bromo-6-methyl-2-oxo-undec-5-ene (10.4 g, 0.04 mole) is dissolved in methylene chloride (100 ml). The solution is cooled to 0° C. and m-chloroperbenzoic acid (7.9 g, 0.04 mole of 85% pure substance) in methylene chloride (180 ml) is added while stirring at +5°-10° C. within 25 minutes. After stirring for 3 hours at 0° C., the reaction mixture is stored at +5° C. for 16 hours. It is then filtered through a sintered glass funnel, and the filtrate is washed first with saturated aqueous sodium bicarbonate, and then 5 times with sodium sulfite (60 g in 500 ml of H2O). The solution is washed with saturated aqueous sodium chloride, dried with sodium sulfate, filtered, and evaporated in vacuo to give 1-bromo-5,6-epoxy-6-methyl-undecan-2-one (10.63 g).

Workup

  1. stirringAfter stirring for 3 hours at 0° C.
  2. waitthe reaction mixture is stored at +5° C. for 16 hours
  3. filtrationIt is then filtered through a sintered glass funnel
  4. washthe filtrate is washed first with saturated aqueous sodium bicarbonate
  5. washThe solution is washed with saturated aqueous sodium chloride
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-c3a156cf030d4520b21615229d43510b
Source dataset
uspto-grants-1981_06
Patent number
US04276216

Reaction notes

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