2-Methoxypropene → HCID 10313515, compound

HRID 844617Notes

Reaction equation

HRID 844617 reaction equation
[CH3:1][C:2](O)([CH2:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9])[C:3]#[CH:4].C[O:13][C:14]([CH3:16])=[CH2:15]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CCCCCCC>[CH3:1][C:2]([CH2:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9])=[C:3]=[CH:4][CH2:15][C:14](=[O:13])[CH3:16]

Participants

5

Reactant 2

HCID 83002-Methoxypropene2×HCID 98128293,7-Dimethyl-1-octyn-3-ol

Product 1

HCID 10313515HCID 10313515, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)Catalyst2×HCID 8900HeptaneSolvent

Procedure

30.9 g 3,7-dimethyl-1-octin-3-ol, 28.9 g isopropenyl methyl ether and 60 ml n-heptane were initially introduced into a 250 ml flask and 25 mg pyridinium toluene-4-sulfonate were then added. The reaction mixture was stirred under reflux for 7 hours. During this period of time, 14.4 g isopropenyl methyl ether and 25 mg pyridinium toluene-4-sulfonate were added in two portions. When the reaction had ended, the solution was evaporated. The residue was distilled in vacuo. 31.9 g 6,10-dimethyl-4,5-undecadien-2-one were obtained, which corresponds to a yield of 82%.

Workup

  1. temperatureunder reflux for 7 hours
  2. customthe solution was evaporated
  3. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-0f6232f7ff82477bb9663487603407f3
Source dataset
uspto-grants-2002_04
Patent number
US06380437B1

Reaction notes

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