Cetyl Alcohol → 8-(Hexadecyloxy)-7-methoxy-1-octene

HRID 1586688Notes

Reaction equation

HRID 1586688 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH:5]([O:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[CH2:25](O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>CN(C)C=O.O>[CH2:40]([O:3][CH2:4][CH:5]([O:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25]

Participants

7

Reactant 4

HCID 2682Cetyl AlcoholHCID 24758Sodium hydrideHCID 85570p-ToluenesulfonateHCID 199395708-Hydroxy-7-methoxy-1-octene

Product 1

HCID 199395658-(Hexadecyloxy)-7-methoxy-1-octene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 7.4 g of 60% sodium hydride in 100 ml of dimethylformamide was added a solution of 8-hydroxy-7-methoxy-1-octene in 150 ml of dimethylformamide over 1.5 hours. A 63.4 g portion of the tosylate of 1-hexadecanol was added and the mixture was stirred for 18 hours, poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was purified by chromatography giving 41.5 g of the title compound as a oil.

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether solution was dried
  3. customevaporated
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-5c72e9d2f180435b91bd3a2cd8be9efb
Source dataset
uspto-grants-1993_06
Patent number
US05215975

Reaction notes

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