Sodium Hydroxide → HCID 53921627, compound

HRID 1658871Notes

Reaction equation

HRID 1658871 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]=[CH:5][CH:6]=[CH:7][CH2:8][CH:9]([CH3:16])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14].ClC1C=CC=C(C(OO)=[O:26])C=1.[OH-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[CH:4]=[CH:5][CH:6]=[CH:7][CH2:8][CH:9]([CH3:16])[CH2:10][CH2:11][CH:12]1[O:26][C:13]1([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 54461647HCID 54461647, compound

Product 1

HCID 53921627HCID 53921627, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.4 g of 7,11-dimethyl-2,4,10-dodecatrienoic acid methyl ester is dissolved in 30 ml of methylene chloride and mixed portionwise at 0°C., with stirring, with 2.4 g of m-chloroperbenzoic acid (ca 80% by wt.). Subsequently the mixture is stirred for a further 1.5 hours at 0°C. The mixture is poured on to ice, treated with 1-N sodium hydroxide, and extracted with diethyl ether. The ethereal phase is washed to neutrality, dried and evaporated. The product is chromatographed on a 50-fold amount of Kieselgel, using hexane/20% by volume ethyl acetate as the eluant. There is obtained 10,11-epoxy-7,11-dimethyl-2,4-dodecadienoic acid methyl ester, as a colorless oil; boiling point ca. 62°C/0.05 mmHg (bulb tube); nD25 = 1.4958.

Workup

  1. additionmixed portionwise at 0°C.
  2. additionThe mixture is poured on to ice
  3. extractionextracted with diethyl ether
  4. washThe ethereal phase is washed to neutrality
  5. customdried
  6. customevaporated
  7. customThe product is chromatographed on a 50-fold amount of Kieselgel

Sources & evidence

ORD record
ord-ecc9dfa7aaa14c7db116c02fea76da6a
Source dataset
uspto-grants-1976_06
Patent number
US03966780

Reaction notes

Loading…