Sodium Hydroxide → HCID 86735208, compound

HRID 1439408Notes

Reaction equation

HRID 1439408 reaction equation
[CH2:1]([O:3][C:4](=[O:16])/[CH:5]=[CH:6]/[CH:7]=[CH:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH3:2].ClC1C=CC=C(C(OO)=O)C=1.[OH-].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:16])/[CH:5]=[CH:6]/[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 86735209HCID 86735209, compound

Product 1

HCID 86735208HCID 86735208, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6 g of 3,7,11-trimethyl-2-cis/trans, 4-cis/trans-dodecatrienoic acid ethyl ester are dissolved in 75 ml of methylene chloride and treated portionwise with stirring at 0° C with 5 g of m-chloroperbenzoic acid (ca 80 percent). The mixture is subsequently stirred for a further 11/2 hours at 0° C. The reaction mixture is poured onto ice and 1-N aqueous sodium hydroxide and extracted with diethyl ether. The ether phase is washed neutral, dried and evaporated. The product is chromatographed on the 50-fold amount of Kieselgel (eluant: hexane 90 percent by volume/ethyl acetate 20 percent by volume). 10,11-Epoxy-3,7,11-trimethyl-2-cis/trans, 4-cis/trans-dodecadienoic acid ethyl ester is obtained as a colorless oil of boiling point about 135° C/0.01 mmHg (bulb:tube); nD20 = 1.4907.

Workup

  1. additiontreated portionwise
  2. extractionextracted with diethyl ether
  3. washThe ether phase is washed neutral
  4. customdried
  5. customevaporated
  6. customThe product is chromatographed on the 50-fold amount of Kieselgel (eluant: hexane 90 percent by volume/ethyl acetate 20 percent by volume)

Sources & evidence

ORD record
ord-2d26c4e66b6d400fbec8a61d5ac718e9
Source dataset
uspto-grants-1977_11
Patent number
US04059600

Reaction notes

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