Water → 6,10,14-Trimethylpentadeca-3,6,9,13-tetraen-2-one

HRID 637571Notes

Reaction equation

HRID 637571 reaction equation
C([CH:4]([CH2:10][CH:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[C:5]([CH3:9])(O)[C:6]#[CH:7])(C)=C.O1C[CH2:23][CH2:22][CH2:21]1.[N+]([O-])([O-])=O.[K+].[OH2:30]>[N+]([O-])([O-])=O.[Ag+]>[CH3:9][C:5](=[CH:4][CH2:10][CH:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:17])[CH3:18])[CH2:6][CH:7]=[CH:21][C:22](=[O:30])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24434Potassium NitrateHCID 53708500HCID 53708500, compound

Product 1

HCID 566146396,10,14-Trimethylpentadeca-3,6,9,13-tetraen-2-one

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

4-Isopropenyl-3,7,11-trimethyl-6,10-dodecadien-1-yn-3-ol (0.260 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 being heated under reflux for 15 hours, the reaction mixture is treated under the conditions described in Example 1. 6,10,14-Trimethyl-3,6,9,13-pentadecatetraen-2-one (0.120 g) is thus obtained, with the following characteristics:

Workup

  1. temperatureAfter being heated
  2. temperatureunder reflux for 15 hours
  3. additionthe reaction mixture is treated under the conditions

Sources & evidence

ORD record
ord-dbb98972a4a54251b691a35db1f953b9
Source dataset
uspto-grants-1985_12
Patent number
US04556742

Reaction notes

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