Phosphorous acid → 2-Hydroxy-4-[3-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yloxy)-2-hydroxypropoxy]benzophenone

HRID 1493427Notes

Reaction equation

HRID 1493427 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH2:17][CH:18]2[O:20][CH2:19]2)[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH:21]1([O:27][N:28]2[C:33]([CH3:35])([CH3:34])[CH2:32][CH:31]([OH:36])[CH2:30][C:29]2([CH3:38])[CH3:37])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.P(O)(O)O>C(OCC)(=O)C>[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH2:17][CH:18]([OH:20])[CH2:19][O:36][CH:31]2[CH2:32][C:33]([CH3:34])([CH3:35])[N:28]([O:27][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:29]([CH3:38])([CH3:37])[CH2:30]2)[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5]

Participants

5

Reactant 3

HCID 107909Phosphorous acidHCID 113228111-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-olHCID 13118721Methanone, [2-hydroxy-4-(oxiranylmethoxy)phenyl]phenyl-

Product 1

HCID 536905502-Hydroxy-4-[3-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yloxy)-2-hydroxypropoxy]benzophenoneYield 2.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5.0 g (18.5 mmol) of 2-hydroxy-4-(2,3-epoxypropoxy)benzophenone and 15.0 g (58.7 mmol) of 1-cyclohexyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidine is heated to 80° and then treated with 0.5 g of phosphorous acid (99%). The reaction mixture is heated at 80°-90° C. for 6 hours, then cooled and dissolved in ethyl acetate (200 ml). The organic solution is washed with saturated sodium bicarbonate solution (100 ml), dried over magnesium sulfate, and evaporated to a yellow oil. Purification by flash chromatography on silica gel to obtain the least polar material formed in the reaction mixture affords approximately 200 mg of the title compound, a yellow glass.

Workup

  1. temperatureis heated to 80°
  2. temperatureThe reaction mixture is heated at 80°-90° C. for 6 hours
  3. temperaturecooled
  4. washThe organic solution is washed with saturated sodium bicarbonate solution (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to a yellow oil
  7. customPurification by flash chromatography on silica gel
  8. customto obtain the least polar material
  9. customformed in the reaction mixture

Sources & evidence

ORD record
ord-95d2aaa57d924b81968a6fff44f0ad46
Source dataset
uspto-grants-1991_06
Patent number
US05021478

Reaction notes

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