HCID 19598126, compound → HCID 10225137, compound

HRID 2256357Notes

Reaction equation

HRID 2256357 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13](=[O:32])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([C:22]34[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]5)[CH2:23]3)[CH2:29]4)[CH:15]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>[Pd].O1CCOCC1>[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH:13]([OH:32])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([C:22]34[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]5)[CH2:23]3)[CH2:29]4)[CH:15]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 19598126HCID 19598126, compound

Product 1

HCID 10225137HCID 10225137, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

1.3 g (2.98 mmol) of 2-hydroxy-4-[[3-(1-adamantyl)-4-methoxybenzoyl]methoxy]benzoic acid, 200 mg of 10% palladium on charcoal and 50 ml of dioxane are introduced into a reactor. The mixture is hydrogenated at room temperature and under a pressure of 7 bar for 4 hours, the catalyst is filtered and washed with 50 ml of THF, and the filtrates are evaporated. The residue obtained is purified by chromatography on a silica column, eluting with a dichloromethane/methanol mixture (98:2). After evaporation of the solvents, 1 g (77%) of the expected acid of melting point 178°-179° C. is collected.

Workup

  1. filtrationthe catalyst is filtered
  2. washwashed with 50 ml of THF
  3. customthe filtrates are evaporated
  4. customThe residue obtained
  5. customis purified by chromatography on a silica column
  6. washeluting with a dichloromethane/methanol mixture (98:2)
  7. customAfter evaporation of the solvents, 1 g (77%) of the expected acid of melting point 178°-179° C.
  8. customis collected

Sources & evidence

ORD record
ord-a27a482befc24238adb655ef03e8a346
Source dataset
uspto-grants-1997_08
Patent number
US05654331

Reaction notes

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