Ethanol → 15-Methyl-8,11,14-eicosatrienoic acid

HRID 1606678Notes

Reaction equation

HRID 1606678 reaction equation
C[CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][CH2:13][CH:14]=[CH:15][CH2:16][CH:17]=[C:18]([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:3]([OH:5])=[O:4].C(O)C.[OH-].[K+]>O>[CH3:24][C:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:17][CH2:16][CH:15]=[CH:14][CH2:13][CH:12]=[CH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:2][C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 54345286HCID 54345286, compound

Product 1

HCID 5367899415-Methyl-8,11,14-eicosatrienoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 1.3 g. of methyl 15-methyl-8,11,14-eicosatrienoic acid, 12.8 ml of 95% ethanol, 1.1 g. of potassium hydroxide and 1.1 ml. of water under a nitrogen atmosphere was heated under reflux for 2hours, then water and Skellysolve "B" (mixed hexanes) were added. The aqueous and organic layers were separated and the aqueous layer was made acid with 3N hydrochloric acid, then extracted with ether. The ether extract was washed with water, then with saturated aqueous sodium chloride, dried over sodium sulfate, and evaporated leaving a residue comprising 15-methyl-8,11,14-eicosatrienoic acid. The residue was distilled in a short path tube at bath temperatures of about 180°C. and a pressure of about 0.007 mm. The distillate was dissolved in 5% ethyl acetate-benzene and chromatographed over 100 g. of acid washed silica gel. Elution with 600 ml. 5%, 500 ml. 10% and 200 ml. 25% ethyl acetate in benzene, then with 100 ml. of ethyl acetate, collecting 50 ml. fractions, and evaporation of the eluate fractions gave a first peak of 183 mg., followed by a 448 mg. peak comprising 15-methyl-8,11,14-eicosatrienoic acid showing one spot on TLC analysis, and having the following NMR absorptions:

Workup

  1. additionA mixture of 1.3 g
  2. temperatureunder reflux for 2hours
  3. additionwere added
  4. customThe aqueous and organic layers were separated
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. washwas washed with water
  8. dry with materialwith saturated aqueous sodium chloride, dried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-51944794580642caa9c57cdd80e63183
Source dataset
uspto-grants-1976_04
Patent number
US03953499

Reaction notes

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