1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-ol → HCID 19831354, compound

HRID 1493415Notes

Reaction equation

HRID 1493415 reaction equation
[C:1]([C:9]1[CH:20]=[CH:19][C:12]([O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=1[OH:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1[CH2:28][C:27]([CH3:30])([CH3:29])[N:26]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:25]([CH3:41])([CH3:40])[CH2:24]1>C1(C)C(C)=CC=CC=1>[OH:21][C:10]1[CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17][CH:18]2[CH2:30][C:27]([CH3:28])([CH3:29])[N:26]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:25]([CH3:40])([CH3:41])[CH2:24]2)=[O:16])[CH:19]=[CH:20][C:9]=1[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:8]

Participants

4

Reactant 2

HCID 113466831-Octyloxy-2,2,6,6-tetramethylpiperidin-4-olHCID 14618907Methyl 4-Benzoyl-3-hydroxyphenoxyacetate

Product 1

HCID 19831354HCID 19831354, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 22.0 g (76.8 mmol) of methyl 4-benzoyl-3-hydroxyphenoxyacetate, 32.9 g (0.115 mol) of 4-hydroxy-1-octyloxy-2,2,6,6-tetramethylpiperidine, and 100 ml of xylene is heated at reflux. Water is removed by fractional distillation. The reaction mixture is cooled to 80° C., treated with 2.1 g of lithium amide, and diluted with 50 ml of xylene. The reaction mixture is heated at reflux for 2 hours, and methanol is removed by fractional distillation. The reaction mixture is cooled, then diluted with diethyl ether (250 ml). The organic solution is washed with 1N hydrochloric acid (200 ml), and solids are removed by filtration. The solution is washed with saturated sodium bicarbonate solution (100 ml), dried over magnesium sulfate, and concentrated to an oil. Purification by flash chromatography on silica gel (85:15 heptane: ethyl acetate) affords 32.6 g (79% yield) of the title compound, a yellow syrup.

Workup

  1. temperatureis heated
  2. temperatureat reflux
  3. customWater is removed by fractional distillation
  4. additiontreated with 2.1 g of lithium amide
  5. additiondiluted with 50 ml of xylene
  6. temperatureThe reaction mixture is heated
  7. temperatureat reflux for 2 hours
  8. custommethanol is removed by fractional distillation
  9. temperatureThe reaction mixture is cooled
  10. additiondiluted with diethyl ether (250 ml)
  11. washThe organic solution is washed with 1N hydrochloric acid (200 ml), and solids
  12. customare removed by filtration
  13. washThe solution is washed with saturated sodium bicarbonate solution (100 ml)
  14. dry with materialdried over magnesium sulfate
  15. concentrationconcentrated to an oil
  16. customPurification by flash chromatography on silica gel (85:15 heptane: ethyl acetate)

Sources & evidence

ORD record
ord-c6c849ec003b4166905c300bee58cc1e
Source dataset
uspto-grants-1991_06
Patent number
US05021478

Reaction notes

Loading…