Toluene → 1-Acetyl-3,3-dimethyl-1-(2-methyl-2-propenyl)cyclohexane

HRID 867149

Reaction equation

HRID 867149 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].[C:19]1(C)[CH:24]=CC=[CH:21][CH:20]=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].[CH3:10][C:6]1([CH3:11])[CH2:7][CH2:8][CH2:9][CH:4]([C:1](=[O:3])[CH:2]([CH2:14][C:15](=[CH2:17])[CH3:16])[CH2:24][CH:19]=[CH:20][CH3:21])[CH2:5]1

Participants

9

Reactant 4

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

Product 3

HCID 913881-(3,3-Dimethylcyclohexyl)ethanoneHCID 203846051-Acetyl-3,3-dimethyl-1-(2-methyl-2-propenyl)cyclohexaneYield 5%HCID 540152333,3-Dimethyl-1-(2-methallyl-5-methyl-4-pentenoyl)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 41/4 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-methallylcyclohexane (104°, 3.0 mm Hg, containing 5% 3,3-dimethyl-(4-methyl-4-pentenoyl)cyclohexane) and 73 grams of 3,3-dimethyl-1-(2-methallyl-5-methyl-4-pentenoyl) cyclohexane. A portion of the latter compound is isolated by GLC chromatography (1' × 1/4 inch 80% SE-30 packed column; 200° C. isothermal) and exhibits the following odor and flavor properties.

Workup

  1. temperatureat reflux for 41/4 hours
  2. distillationthe organic layer is distilled rapidly through a short column

Sources & evidence

ORD record
ord-0df0f149293c4311a0c530a892b4933b
Source dataset
uspto-grants-1978_07
Patent number
US04102928

Linked notes

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