Dicyclohexylamine → 3-Hydroxy-2-cyclobuten-1-one dicyclohexylammonium salt

HRID 1534185Notes

Reaction equation

HRID 1534185 reaction equation
[CH:1]1([NH:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:14]1(=[O:19])[CH2:17][C:16](=[O:18])[CH2:15]1>C(OCC)(=O)C>[CH:8]1([NH2+:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1.[OH:19][C:14]1[CH2:17][C:16](=[O:18])[CH:15]=1

Participants

4

Reactant 2

HCID 7582DicyclohexylamineHCID 27357Cyclobutane-1,3-dione

Product 1

HCID 198960263-Hydroxy-2-cyclobuten-1-one dicyclohexylammonium saltYield 102%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 7.1 g of dicyclohexylamine (98 percent; 38.3 mmol) in 15 ml of ethyl acetate was instilled in a suspension of 3.0 g of 1,3-cyclobutanedione (97 percent; 34.6 mmol) in ethyl acetate (52.2 ml) at 20° C. in 15 minutes. After 1 hour of stirring at room temperature, the suspension was washed four times with ethyl acetate and dried under vacuum. 9.4 g of the title product with a content of 94.7 percent (according to HPLC), corresponding to a yield of 96.7 percent, relative to cyclobutanedione, was obtained. Data for the title compound was:

Workup

  1. washthe suspension was washed four times with ethyl acetate
  2. customdried under vacuum

Sources & evidence

ORD record
ord-a41f420c38df46f69cdcd0c308051753
Source dataset
uspto-grants-1992_02
Patent number
US05087756

Reaction notes

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