Ethylene Glycol → 1,5-Dioxa-9-azaspiro[5.5]undecane, 8,8,10,10-tetramethyl-

HRID 133728

Reaction equation

HRID 133728 reaction equation
P(=O)(O)(O)O.[CH3:6][C:7]1([CH3:16])[NH:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:9](=[O:10])[CH2:8]1.[CH2:17]([OH:20])[CH2:18]O.O.[C:22]1(C)C=CC=CC=1>>[CH3:6][C:7]1([CH3:16])[NH:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:9]2([O:20][CH2:17][CH2:18][CH2:22][O:10]2)[CH2:8]1

Participants

6

Reactant 5

HCID 174Ethylene GlycolHCID 962WaterHCID 1004Phosphoric Acid2×HCID 1140TolueneHCID 132202,2,6,6-Tetramethyl-4-piperidone

Product 1

HCID 119617861,5-Dioxa-9-azaspiro[5.5]undecane, 8,8,10,10-tetramethyl-

Procedure

Use of Phosphoric Acid 77 g of triacetonamine were initially charged in 240 g of toluene together with 47 g of ethylene glycol. Subsequently, sufficient phosphoric acid (63 g) was added that the reaction mixture showed an acidic pH (≦2) when tested with a moistened indicator paper. The reaction mixture was heated to reflux temperature and water of reaction formed was removed on a water separator. After approx. 3 hours, there was less than 10% of the desired product according to the gas chromatogram. Instead, a plurality of secondary components had formed which were not investigated further.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customformed
  4. customwas removed on a water separator
  5. customInstead, a plurality of secondary components had formed which

Sources & evidence

ORD record
ord-7875deca30664fefb1e356d47aae5457
Source dataset
uspto-grants-2008_06
Patent number
US07390930B2

Linked notes

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