HCID 5363514, compound → HCID 54300712, compound

HRID 2254513Notes

Reaction equation

HRID 2254513 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[CH:16]=[CH:17]/[CH3:18])(=O)C.O1CCCCC1OCCCCCCCCCC=CC=CC>CO.O>[CH2:5]([OH:4])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][CH:16]=[CH:17][CH3:18]

Participants

5

Reactant 2

HCID 5363514HCID 5363514, compoundHCID 54384297HCID 54384297, compound

Product 1

HCID 54300712HCID 54300712, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 962WaterSolvent

Procedure

To prepare (E,E)-10,12-tetradecadien-1-ol acetate (I), the tetradecadiene (D) (5.6 g) in 200 ml methanol containing eight drops concentrated HCl was refluxed for 15 minutes. After the solution was cooled, 400 ml of water was added, and the mixture was extracted three times with hexane. The hexane extract was dried over sodium sulfate, and the hexane was removed with a rotary evaporator leaving 3 g crude 10,12-tetradecadienol, which was purified by silica gel liquid chromatography. Unwanted side products were eluted with 10% ether/hexane, and the alcohol was eluted with 50% ether/hexane, giving 2.4 g (66% yield based on the dodecenenitrile (B)).

Workup

  1. temperatureAfter the solution was cooled
  2. extractionthe mixture was extracted three times with hexane
  3. extractionThe hexane extract
  4. dry with materialwas dried over sodium sulfate
  5. customthe hexane was removed with a rotary evaporator

Sources & evidence

ORD record
ord-82c567ad6cf846f2abc88540e400232e
Source dataset
uspto-grants-1993_08
Patent number
US05236715

Reaction notes

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