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

HRID 35957
Notes
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Reaction equation

HRID 35957 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962WaterSolvent
HCID 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-95f61b892d9b4419a2ca820c0f9db754
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05411983

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes