Ethanol → 3-Hydroxy-2-cyclobuten-1one-dicyclohexylmethyl ammonium salt

HRID 892662Notes

Reaction equation

HRID 892662 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([CH:19]([NH2:26])[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(OCC)(=O)C>[CH:13]1([CH:19]([NH3+:26])[CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[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 10774245alpha-CyclohexylcyclohexanemethanamineHCID 108554523-Acetoxy-2-cyclobuten-1-one

Product 1

HCID 867454593-Hydroxy-2-cyclobuten-1one-dicyclohexylmethyl ammonium saltYield 45.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3.24 g of 3-acetoxy-2-cyclobuten-1-one (triketene, 97.5 percent; 25.0 mmol) was dissolved in 1.9 g of ethanol (41.3 mmol) and 40 g of ethyl acetate. 9.83 g of dicyclohexylmethylamine (98.9 percent; 50.0 mmol), dissolved in 10 g of ethyl acetate, was instilled in this solution at 20° C. in 15 minutes and stirred for 1 hour at room temperature. After another hour of stirring at 5° C., the suspension was filtered and dried under vacuum. 3.21 g of the title product with a content of 94.5 percent (according to HPLC), corresponding to a yield of 43.5 percent, relative to the 3-acetoxy-2-cyclobuten-1-one, was obtained. Data for the title compound was:

Workup

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

Sources & evidence

ORD record
ord-42cafcf3e3a34effb04f14e45413fb31
Source dataset
uspto-grants-1992_06
Patent number
US05118861

Reaction notes

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