1,3-Cyclohexanedione → HCID 69916320, compound

HRID 2306542Notes

Reaction equation

HRID 2306542 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH2:12][CH:13]2[CH2:16][CH2:15][CH2:14]2)=[C:9]([Br:17])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:18]1(=O)[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH2:19]1.Cl.CN(C)CCCN=C=NCC.CN(C1C=CC=CN=1)C>C(Cl)Cl>[Br:1][C:2]1[C:10]([O:11][CH2:12][CH:13]2[CH2:14][CH2:15][CH2:16]2)=[C:9]([Br:17])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:18]1[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH:19]=1)=[O:5]

Participants

6

Reactant 4

HCID 104341,3-CyclohexanedioneHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15906664HCID 15906664, compound

Product 1

HCID 69916320HCID 69916320, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.150 g (3.20 mmol) of 2,4-dibromo-3-(cyclobutylmethoxy)benzoic acid, 0.39 g (3.50 mmol) of cyclohexane-1,3-dione, 0.618 g (3.20 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 0.004 g of dimethylaminopyridine were stirred for 10 hours at room temperature in 30 ml of methylene chloride. The mixture was subsequently diluted with methylene chloride and washed with 0.5 N HCl, with water, with saturated NaHCO3 solution and again with water. After the combined organic phases had been dried over Na2SO4 and evaporated completely on a rotary evaporator, 3-oxo-1-cyclohexenyl 2,4 dibromo-3-cyclobutylmethoxybenzoate was obtained in the form of a yellow resin.

Workup

  1. washwashed with 0.5 N HCl, with water, with saturated NaHCO3 solution and again with water
  2. dry with materialAfter the combined organic phases had been dried over Na2SO4
  3. customevaporated completely on a rotary evaporator

Sources & evidence

ORD record
ord-506210f0f8df40c8ae5fb101a3fb5300
Source dataset
uspto-grants-2004_12
Patent number
US06828276B2

Reaction notes

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