Water → HCID 54328416, compound

HRID 637573Notes

Reaction equation

HRID 637573 reaction equation
[CH:1]([C:5](O)([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])C#C)=[C:2]([CH3:4])[CH3:3].O1CC[CH2:16][CH2:15]1.[N+]([O-])([O-])=O.[K+].[OH2:24]>[N+]([O-])([O-])=O.[Ag+]>[CH3:4][C:2]([CH2:1][CH:5]=[CH:8][C:9](=[O:24])[CH2:10][CH2:11][CH2:12][CH2:15][CH3:16])=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24434Potassium NitrateHCID 20257144HCID 20257144, compound

Product 1

HCID 54328416HCID 54328416, compound

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst2×

Procedure

3-Isobutenyl-1-octyn-3-ol (0.180 g; 10-3 mole) is kept at the reflux temperature of tetrahydrofuran and protected from light, in the presence of silver nitrate (0.017 g; 10-4 mole) and potassium nitrate (0.101 g; 10-3 mole) in a mixture (6 cc) of tetrahydrofuran and water (2:1 by volume). After 6 hours of reaction silver nitrate (0.017 g) is again added. Refluxing is continued for another 8.5 hours and the reaction mixture is then treated under the conditions described in Example 1. 2-Methyl-1,4-undecadien-6-one (0.104 g) is obtained.

Workup

  1. additionis again added
  2. temperatureRefluxing
  3. additionthe reaction mixture is then treated under the conditions

Sources & evidence

ORD record
ord-e52e8b417a834083bd08a2d39d4062eb
Source dataset
uspto-grants-1985_12
Patent number
US04556742

Reaction notes

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