Diethylamine → 3-Hydroxy-2-cyclobuten-1-one-diethylammonium salt

HRID 892658Notes

Reaction equation

HRID 892658 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C([O:9][C:10]1[CH2:13][C:12](=[O:14])[CH:11]=1)(=O)C>C(OCC)(=O)C>[CH2:1]([NH2+:3][CH2:4][CH3:5])[CH3:2].[OH:14][C:12]1[CH2:13][C:10](=[O:9])[CH:11]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 108554523-Acetoxy-2-cyclobuten-1-one

Product 1

HCID 198960273-Hydroxy-2-cyclobuten-1-one-diethylammonium saltYield 94.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 3.67 g of diethylamine (99.5 percent; 50.0 mmol) in 10 g of ethyl acetate was instilled in a solution of 3.25 g of 3-acetoxy-2-cyclobuten-1-one (triketene, content, 97 percent; 25.0 mmol) in 40 g of ethyl acetate at 20° C. within 18 minutes. The reaction mixture was stirred for another hour at room temperature, then filtered and dried under vacuum. 3.75 g of the title product with a purity of 94.1 percent (according to HPLC), corresponding to a yield of 89.8 percent, relative to the 3-acetoxy-2-cyclobuten-1-one, was obtained. Data for the title compound was:

Workup

  1. filtrationfiltered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-80c067dd3c67497294912f86e3d78d59
Source dataset
uspto-grants-1992_06
Patent number
US05118861

Reaction notes

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