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

HRID 46998

Reaction equation

HRID 46998 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].[CH2:12](Cl)[C:13](=[CH2:15])[CH3:14].C(N(CC)CC)C>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([CH2:14][C:13]([CH3:15])=[CH2:12])[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])[CH2:2][CH2:14][C:13]([CH3:15])=[CH2:12])[CH2:5]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 112413-Chloro-2-methyl-1-propeneHCID 913881-(3,3-Dimethylcyclohexyl)ethanone

Product 3

HCID 913881-(3,3-Dimethylcyclohexyl)ethanoneHCID 203846051-Acetyl-3,3-dimethyl-1-(2-methyl-2-propenyl)cyclohexaneHCID 203846063,3-Dimethyl-1-(4-methyl-4-pentenoyl)cyclohexane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-acetyl-3,3-dimethylcyclohexane (156 grams, 1 mole) sodium hydroxide (60 grams, 1.5 moles), methallyl chloride (135 grams, 1.5 moles) and triethylamine (10 grams) is stirred and heated at 80°-84° C. for 12 hours. The reaction mass is cooled to room temperature. Water is added with stirring, and the aqueous layer is discarded. The organoc layer is distilled to afford 1-acetyl-3,3-dimethylcyclohexane (62.4 gm), 1-acetyl-3,3-dimethyl-1-(2-methyl-2-propenyl)cyclohexane (80 gm), (NMR spectrum, FIG. 1; IR spectrum, FIG. 2), and 3,3-dimethyl-1-(4-methyl-4-pentenoyl)cyclohexane (8 gm).

Workup

  1. temperatureheated at 80°-84° C. for 12 hours
  2. stirringwith stirring
  3. distillationThe organoc layer is distilled

Sources & evidence

ORD record
ord-0f5ca3948f9047739cd0fa00c21693b7
Source dataset
uspto-grants-1979_11
Patent number
US04175569

Linked notes

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