Cyclobutane-1,3-dione → 3-Hydroxy-2-cyclobuten-1one-dicyclohexylmethyl ammonium salt

HRID 892661Notes

Reaction equation

HRID 892661 reaction equation
[CH:1]1([CH:7]([NH2:14])[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:15]1(=[O:20])[CH2:18][C:17](=[O:19])[CH2:16]1>C(OCC)(=O)C>[CH:1]1([CH:7]([NH3+:14])[CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:20][C:15]1[CH2:18][C:17](=[O:19])[CH:16]=1

Participants

4

Reactant 2

HCID 27357Cyclobutane-1,3-dioneHCID 10774245alpha-Cyclohexylcyclohexanemethanamine

Product 1

HCID 867454593-Hydroxy-2-cyclobuten-1one-dicyclohexylmethyl ammonium saltYield 81.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4.99 g of dicyclohexylmethylamine 25.0 mmol) in 10 g of ethyl acetate was instilled in a suspension of 2.11 g of 1,3 cyclobutanedione (23.0 mmol]at 20° C. and stirred for 1 hour. After another 30 minutes of stirring at 5° C., the suspension was filtered and dried under vacuum. 5.53 g of the title product with a purity of 94.7 percent (according to HPLC), corresponding to a yield of 81.4 percent, relative to the cyclobutanedione, was obtained. Data for the title compound was:

Workup

  1. stirringAfter another 30 minutes of stirring at 5° C.
  2. filtrationthe suspension was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-8cc13e468baf44e29747cc8e1721e22a
Source dataset
uspto-grants-1992_06
Patent number
US05118861

Reaction notes

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