Ethanol → 3-Hydroxy-2-cyclobuten-1-one-cyclohexyldimethylammonium salt

HRID 892660Notes

Reaction equation

HRID 892660 reaction equation
C([O:4][C:5]1[CH2:8][C:7](=[O:9])[CH:6]=1)(=O)C.C(O)C.[CH:13]1([N:19]([CH3:21])[CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(OCC)(=O)C>[CH:13]1([NH+:19]([CH3:21])[CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[OH:9][C:7]1[CH2:8][C:5](=[O:4])[CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 7415N,N-DimethylcyclohexylamineHCID 108554523-Acetoxy-2-cyclobuten-1-one

Product 1

HCID 198960323-Hydroxy-2-cyclobuten-1-one-cyclohexyldimethylammonium saltYield 77.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3.24 g of 3-acetoxy-2-cyclobuten-1-one (triketene, 25.0 mmol) was dissolved in I.90 g of absolute ethanol (41.3 mmol) and 40 g of ethyl acetate. 6.45 g of cyclohexyl-dimethylamine (99 percent; 50.0 mmol), dissolved in 10 g of ethyl acetate, was instilled in this solution at 20° C. within 20 minutes. After 2 hours of stirring at room temperature, the suspension was filtered and dried under vacuum. 4.09 g of the title product with a content of 94.5 percent (according to HPLC), corresponding to a yield of 73.2 percent, relative to the 3-acetoxy-2-cyclobuten-1-one (triketene), was obtained. Data for the title compound was:

Workup

  1. filtrationthe suspension was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-a32283585fa44234b5e64769c1a36085
Source dataset
uspto-grants-1992_06
Patent number
US05118861

Reaction notes

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