Benzyl Chloride → 3,7-Dimethyl-1,6-octadien-3-yl 3-oxo-2-benzylbutyrate

HRID 634593Notes

Reaction equation

HRID 634593 reaction equation
C(=O)([O-])[O-].[K+].[K+].[O:7]=[C:8]([CH3:23])[CH2:9][C:10]([O:12][C:13]([CH3:22])([CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH:14]=[CH2:15])=[O:11].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(C)=O>[O:7]=[C:8]([CH3:23])[CH:9]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:10]([O:12][C:13]([CH3:22])([CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH:14]=[CH2:15])=[O:11]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 11791251Linalyl acetoacetate

Product 1

HCID 212602353,7-Dimethyl-1,6-octadien-3-yl 3-oxo-2-benzylbutyrate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (3.92 g, 0.028 mol), 3,7-dimethyl-1,6-octadien-3-yl 3-oxo-butyrate (4.80 g, 0.030 mol), benzyl chloride (4.80 g, 0.038 mol) and acetone (15 mL) are placed in a 50 mL round-bottomed flask fitted with a magnetic stirrer, condenser and argon inlet. The mixture is heated to reflux for 18 h. The cooled mixture is filtered and concentrated by rotary evaporation. The resulting oil is purified on silica gel to yield the desired compound. Structure is confirmed by thin layer chromatography and 1H and 13C NMR.

Workup

  1. customfitted with a magnetic stirrer, condenser and argon inlet
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 18 h
  4. filtrationThe cooled mixture is filtered
  5. concentrationconcentrated by rotary evaporation
  6. customThe resulting oil is purified on silica gel

Sources & evidence

ORD record
ord-6e4cdc18c0c44898b142ffc4459edeb5
Source dataset
uspto-grants-2001_02
Patent number
US06184188B2

Reaction notes

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