Ethylene Glycol → 7,7,9,9-Tetramethyl-8-phenyl-1,4-dioxa-8-phosphaspiro[4.5]decane

HRID 1719408Notes

Reaction equation

HRID 1719408 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:16]1([P:22]2[C:27]([CH3:29])([CH3:28])[CH2:26][C:25](=O)[CH2:24][C:23]2([CH3:32])[CH3:31])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:2]1[CH2:1][O:4][C:25]2([CH2:26][C:27]([CH3:29])([CH3:28])[P:22]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:23]([CH3:32])([CH3:31])[CH2:24]2)[O:3]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 41304594-Phosphorinanone, 2,2,6,6-tetramethyl-1-phenyl-

Product 1

HCID 133084397,7,9,9-Tetramethyl-8-phenyl-1,4-dioxa-8-phosphaspiro[4.5]decaneYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A flask equipped with a Dean-Stark trap was charged with a mixture of 150 mls of ethylene glycol, 0.73 grams p-toluenesulfonic acid and 800 mls toluene and then purged with nitrogen for one hour. To this mixture, 10 grams of 1-phenyl-2,2,6,6-tetramethyl-4-phosphorinanone (0.04 mole) were added. The two phase system was heated to reflux and 26 mls of a water-ethylene glycol azeotrope were collected over a 20 hour period. The reaction mixture was washed with saturated sodium bicarbonate, water, dried over anhydrous potassium carbonate, the solvent removed in vacuo, and the residue distilled under reduced pressure to give 9.2 grams (78%) of a colorless liquid, bp 134°-140° C. (0.3 mm Hg).

Workup

  1. customA flask equipped with a Dean-Stark trap
  2. custompurged with nitrogen for one hour
  3. temperatureThe two phase system was heated
  4. temperatureto reflux
  5. custom26 mls of a water-ethylene glycol azeotrope were collected over a 20 hour period
  6. washThe reaction mixture was washed with saturated sodium bicarbonate, water
  7. dry with materialdried over anhydrous potassium carbonate
  8. customthe solvent removed in vacuo
  9. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-0e69647977a84ae8a8b0fec34a77c560
Source dataset
uspto-grants-1985_09
Patent number
US04539421

Reaction notes

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