Toluene → 1-(3,3-Dimethylcyclohexyl)-pent-4-en-1-one

HRID 867152

Reaction equation

HRID 867152 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-].[K+].[C:14]1(C)[CH:19]=CC=C[CH:15]=1.[CH2:21](Cl)[CH:22]=[CH2:23]>O>[C:1]([CH2:4][CH2:5][C:6]([CH3:10])([CH3:11])[CH2:7][CH2:8][CH3:9])(=[O:3])[CH3:2].[C:1]([C:4]1([CH2:19][CH:14]=[CH2:15])[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][CH2:23][CH:22]=[CH2:21])[CH2:5]1

Participants

8

Reactant 4

HCID 1140TolueneHCID 7850Allyl chlorideHCID 14797Potassium HydroxideHCID 913881-(3,3-Dimethylcyclohexyl)ethanone

Product 3

HCID 64534231-(3,3-Dimethylcyclohexyl)-pent-4-en-1-oneHCID 148178511-[3,3-Dimethyl-1-(prop-2-en-1-yl)cyclohexyl]ethan-1-oneHCID 20317600HCID 20317600, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A slurry of 1-acetyl-3,3-dimethylcyclohexane (156 grams, 1 mole), potassium hydroxide (86 grams, 1.5 moles), and toluene (300 ml) is heated to reflux. Allyl chloride (114 grams, 1.5 moles) is added to the thickened reaction mass whereupon the mass becomes more fluid. The mixture is heated at reflux for 61/2 hours. At the end of this period, the reaction mass is cooled to room temperature, and 500 ml of water is added thereto. The aqueous layer is discarded, and the organic layer is distilled to afford 74 grams of recovered 1-acetyl-3,3-dimethyl hexane, 53 grams of 1-acetyl-3,3-dimethyl-1-(2-propenyl) cyclohexane, and 35 grams of 3,3-dimethyl-1-(4-pentenoyl) cyclohexane.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 61/2 hours
  3. distillationthe organic layer is distilled

Sources & evidence

ORD record
ord-1f6a393529744b2383390b63bdc38053
Source dataset
uspto-grants-1978_07
Patent number
US04102928

Linked notes

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