Benzyl Chloride → HCID 12434856, compound

HRID 1494695Notes

Reaction equation

HRID 1494695 reaction equation
[OH-].[Na+].[CH3:3][C:4]([CH3:9])=[CH:5][C:6](=[O:8])[CH3:7].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O.[Cl-].C([N+](CC)(CC)CCCCCCCCCCCC)C>[CH2:10]([C:5](=[C:4]([CH3:9])[CH3:3])[C:6](=[O:8])[CH3:7])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 8858Mesityl oxideHCID 14798Sodium Hydroxide

Product 1

HCID 12434856HCID 12434856, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 3015159N,N,N-Triethyldodecan-1-aminium chlorideCatalystHCID 962WaterSolvent2×

Procedure

A solution of 2.7 g (65 millimole) of NaOH in 2.5 ml of water was added to 8.5 g (90 millimole) of 4-methyl-3-pentene-2-one and stirred at 40° C. while 200 mg of triethyldodecyl ammonium chloride was added. The red solution was treated with 5.4 g (45 millimole) of benzyl chloride and the stirring continued for 4 hours at 50° C. The resulting yellow brown solution was cooled to room temperature and diluted with 10 ml of water, followed by extraction with 50 ml of ether. The organic extract was washed with 10 ml of water, 10 ml of 10% HCl, and then another 10 ml of water, followed by drying over magnesium sulfate. Evaporation of solvent and flash column chromatography gave 4.4 g (52% yield) of 3-benzyl-4-methyl-3-pentene-2-one.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with 50 ml of ether
  3. extractionThe organic extract
  4. washwas washed with 10 ml of water, 10 ml of 10% HCl
  5. dry with materialby drying over magnesium sulfate
  6. customEvaporation of solvent and flash column chromatography

Sources & evidence

ORD record
ord-0c8e882893604bbe8af3f50f114be88d
Source dataset
uspto-grants-1991_06
Patent number
US05026918

Reaction notes

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