Water → CID 559558

HRID 1789252Notes

Reaction equation

HRID 1789252 reaction equation
C([O:3][C:4](=O)[CH:5]=[CH:6][CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:4]([OH:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH:11][CH2:12][CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride4×HCID 54247501Ethyl hexadeca-2,4-dienoate

Product 1

HCID 559558CID 559558Yield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
0 °C

Procedure

The ethylhexadecadienoate was reduced with lithium aluminum hydride (LAH) in tetrahydrofuran as follows. An oven dried 3-neck flask equipped with a magnetic stirrer, reflux condenser and an addition funnel was charged with 2 equivalents of LAH in dry tetrahydrofuran (THF). The reaction vessel and contents were maintained under a positive flow of nitrogen as 1 equivalent of ester (ethylhexadecadienoate) dissolved in an equal volume of dry THF was added dropwise to the stirred LAH suspension at a rate to maintain the THF at a gentle boil. After ester addition was complete, the reaction mixture was refluxed gently for an additional 2 hours, cooled to 0° C. and one equivalent of water slowly added to decompose excess LAH, followed by addition of 15% aqueous NaOH. The resulting gray gel was filtered and the organic layer washed with water, dried over adsorbent and concentrated on a rotary evaporator. Yields of about 41% of the desired 7,11-hexadecadien-1-ol were obtained.

Workup

  1. customAn oven dried 3-neck flask
  2. customequipped with a magnetic stirrer
  3. temperaturereflux condenser and an addition funnel
  4. temperaturethe reaction mixture was refluxed gently for an additional 2 hours
  5. filtrationThe resulting gray gel was filtered
  6. washthe organic layer washed with water
  7. customdried over adsorbent and
  8. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-04dbb461ed174b00a6244db67ec1e09f
Source dataset
uspto-grants-1987_08
Patent number
US04687867

Reaction notes

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