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

HRID 1534186Notes

Reaction equation

HRID 1534186 reaction equation
C([O:4][C:5]1[CH2:8][C:7](=[O:9])[CH:6]=1)(=O)C.[CH:10]1([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>>[CH:17]1([NH2+:16][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1.[OH:9][C:7]1[CH2:8][C:5](=[O:4])[CH:6]=1

Participants

3

Reactant 2

HCID 7582DicyclohexylamineHCID 108554523-Acetoxy-2-cyclobuten-1-one

Product 1

HCID 198960263-Hydroxy-2-cyclobuten-1-one dicyclohexylammonium saltYield 111.8%

Procedure

1000 g of distillation residue from diketene production, containing 22.0 percent of 3-acetoxy-2-cyclobuten-1-one (1.74 mol), was dissolved in 1078 ml of (970 g). 707.4 g of dicyclohexylamine (98 percent; 3.81 mol) was instilled in this black solution at 10° C. within 60 minutes. After 90 minutes, of stirring at +10° C., the suspension was filtered, suspended three times with ethyl acetate and dried under vacuum. 518 g of the title product with a content of 65.5 percent (HPLC), corresponding to a yield of 73.4 percent, relative to 3-acetoxy-2-cyclobuten-1-one, was obtained. Data for the title compound was:

Workup

  1. distillation1000 g of distillation residue from diketene production
  2. dissolutionwas dissolved in 1078 ml of (970 g)
  3. filtrationthe suspension was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e353f647d3634583991b20bddd031b45
Source dataset
uspto-grants-1992_02
Patent number
US05087756

Reaction notes

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