Allyl chloride → 1-(3,3-Dimethylcyclohexyl)ethanone

HRID 867153Notes

Reaction equation

HRID 867153 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)[CH:15]=[CH2:16].[CH2:18](N(CC)CC)[CH3:19]>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][CH:15]=[CH:16][CH2:18][CH3:19])[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][CH2:16][CH:15]=[CH2:14])[CH2:5]1

Participants

8

Reactant 4

HCID 7850Allyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 913881-(3,3-Dimethylcyclohexyl)ethanone

Product 3

HCID 913881-(3,3-Dimethylcyclohexyl)ethanoneHCID 64534231-(3,3-Dimethylcyclohexyl)-pent-4-en-1-oneHCID 537246071-Acetyl-3,3-dimethyl-1-(2-pentenyl) 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), allyl chloride (114 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 organic layer is distilled to afford 119 grams of 1-acetyl-3,3-dimethylcyclohexane, 31 grams of 1-acetyl-3,3-dimethyl-1-(2-pentenyl) cyclohexane, and 5 grams of 3,3-dimethyl-1-(4-pentenoyl) cyclohexane.

Workup

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

Sources & evidence

ORD record
ord-eea4779a8076450b860971bd9ec322b9
Source dataset
uspto-grants-1978_07
Patent number
US04102928

Reaction notes

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