Benzyl Chloride → 1-Benzyloxy-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraene

HRID 358510Notes

Reaction equation

HRID 358510 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([CH2:14][CH2:15][CH:16]=[C:17]([CH3:29])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])=[CH:11][CH2:12][OH:13].[OH-].[K+]>CCCCCC>[CH2:1]([O:13][CH2:12][CH:11]=[C:10]([CH3:9])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:29])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 14797Potassium HydroxideHCID 65183Tetraprenol

Product 1

HCID 545558871-Benzyloxy-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraeneYield 61%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To 100 ml of benzyl chloride were added 15 g of 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-ol and 6.0 g of finely divided potassium hydroxide, and the resulting mixture was refluxed under stirring for 2 hours. The mixture was cooled and then to the mixture was added 1 liter of hexane. The hexane solution was then washed with water and concentrated. The concentrate was purified over a silica gel column to give 12 g of 1-benzyloxy-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraene (yield 61%).

Workup

  1. temperaturethe resulting mixture was refluxed
  2. temperatureThe mixture was cooled
  3. washThe hexane solution was then washed with water
  4. concentrationconcentrated
  5. customThe concentrate was purified over a silica gel column

Sources & evidence

ORD record
ord-d08294c6c15c48189a0a4ad06df5a438
Source dataset
uspto-grants-1984_08
Patent number
US04468458

Reaction notes

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