1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → HCID 54127819, compound

HRID 1584552Notes

Reaction equation

HRID 1584552 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].C[O:14][CH2:15][CH2:16][O:17][CH2:18][C:19]([O:21][CH3:22])=O>CCCCCCC>[CH3:22][O:21][CH2:19][CH2:18][O:17][CH2:16][C:15]([O:10][CH:5]1[CH2:6][C:7]([CH3:8])([CH3:9])[N:2]([OH:1])[C:3]([CH3:12])([CH3:11])[CH2:4]1)=[O:14]

Participants

4

Reactant 2

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 28661Methyl 2-(2-methoxyethoxy)acetate

Product 1

HCID 54127819HCID 54127819, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

34.4 grams of 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine, 29.6 grams of methyl 2-methoxyethoxyacetate and 300 mL of heptane are transferred to a 500 mL 3-necked, round-bottomed flask equipped with a mechanical stirrer, Dean-Stark trap and condenser. Trace amounts of water are removed by azeotropic distillation. 0.25 mL of tetraisopropyl orthotitanate is added to the reaction mixture. The reaction mixture is refluxed for six hours and the liberated methanol is collected in the Dean-Stark trap. The reaction mixture is allowed to cool and is then partitioned between 300 mL of ethyl acetate and 300 mL of water. The phases are separated and the organic phase is washed with water and dried over anhydrous magnesium sulfate. Evaporation of the solvent leaves the title compound as a red oil.

Workup

  1. customround-bottomed flask equipped with a mechanical stirrer
  2. customTrace amounts of water are removed by azeotropic distillation
  3. addition0.25 mL of tetraisopropyl orthotitanate is added to the reaction mixture
  4. temperatureThe reaction mixture is refluxed for six hours
  5. customthe liberated methanol is collected in the Dean-Stark trap
  6. temperatureto cool
  7. customis then partitioned between 300 mL of ethyl acetate and 300 mL of water
  8. customThe phases are separated
  9. washthe organic phase is washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customEvaporation of the solvent

Sources & evidence

ORD record
ord-9da6d133999e42c88edf22184f10780a
Source dataset
uspto-grants-1999_08
Patent number
US05932735

Reaction notes

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