Acetaldehyde → 2-Ethylcyclohexane-1,3-dione

HRID 1519401Notes

Reaction equation

HRID 1519401 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[CH3:9][CH:10]=O.CCOC(C1CC(C(OCC)=O)=C(C)NC=1C)=O.N1C=CC=CC=1>CO.C(Cl)Cl>[CH2:9]([CH:2]1[C:3](=[O:7])[CH2:4][CH2:5][CH2:6][C:1]1=[O:8])[CH3:10]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 1049PyridineHCID 104341,3-CyclohexanedioneHCID 70849Hantzsch ester

Product 1

HCID 108988052-Ethylcyclohexane-1,3-dioneYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1,3-Cyclohexanedione (10 g, 89.2 mmol), 40% aqueous CH3CHO (49.4 g, 445.9 mmol) were dissolved in methanol (40 mL) followed by addition of Hantzsch ester (22.7 g, 89.2 mmol) and pyridine (2.1 g, 18.74 mmol) under nitrogen. The resulting light yellow mixture was stirred at room temperature overnight, then concentrated to give crude product that was re-slurried in a mixture of CH2Cl2 (40 mL) and hexanes (60 mL) to furnish 2-ethyl-1,3-cyclohexanedione (8.6 g, 69%).

Workup

  1. concentrationconcentrated
  2. customto give crude product that

Sources & evidence

ORD record
ord-0be1b85333fe4f2e857f2598abcd2658
Source dataset
uspto-grants-2015_07
Patent number
US09073888B2

Reaction notes

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