Toluene → 1-(3,3-Dimethylcyclohexyl)ethanone

HRID 46997

Reaction equation

HRID 46997 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][C:6]([CH3:11])([CH3:10])[CH2:5]1)(=[O:3])[CH3:2].[OH-].[Na+].[CH2:14](Cl)[C:15](=[CH2:17])[CH3:16].C1(C)C=CC=CC=1>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][C:6]([CH3:11])([CH3:10])[CH2:5]1)(=[O:3])[CH3:2].[C:1]([C:4]1([CH2:16][C:15](=[CH2:14])[CH3:17])[CH2:9][CH2:8][CH2:7][C:6]([CH3:11])([CH3:10])[CH2:5]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 1140TolueneHCID 112413-Chloro-2-methyl-1-propeneHCID 14798Sodium HydroxideHCID 913881-(3,3-Dimethylcyclohexyl)ethanone

Product 2

HCID 913881-(3,3-Dimethylcyclohexyl)ethanoneHCID 203846051-Acetyl-3,3-dimethyl-1-(2-methyl-2-propenyl)cyclohexane

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A slurry of 1-acetyl-3,3-dimethylcyclohexane (624 grams, 4 moles), granular sodium hydroxide (240 grams, 6 moles), Aliquot® 336 (tricaprylmethylammonium chloride [35 grams]), methallyl chloride (432 grams, 4.8 moles), and 400 ml of toluene is heated at reflux for 4 1/4 hours. At the end of this time, one liter of water is added to the cooled reaction mass. The aqueous layer is discarded, and the organic layer is distilled rapidly through a short column to afford 203 grams of recovered 1-acetyl-3,3,-dimethylcyclohexane, 500 grams of 1-acetyl-3,3-dimethyl-1-methallyl cyclohexane, and 73 grams of 3,3-dimethyl-1-(2-methyllyl-5-methyl-4-pentenoyl)cyclohexane) (1°-4°, 3.0 mm Hg) containing 5% of 3,3-dimethyl-1-(4-methyl-4-pentenoyl). A portion of the latter compound is isolated by GLC chromatography (1'×1/4" 80% SE-30 packed column; 200° C. isothermal) and exhibits the following odor and flavor properties:

Workup

  1. temperatureat reflux for 4 1/4 hours
  2. distillationthe organic layer is distilled rapidly through a short column

Sources & evidence

ORD record
ord-5abf4bc882194c00b49013a92b58a98e
Source dataset
uspto-grants-1979_11
Patent number
US04175569

Linked notes

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