HCID 21474543, compound → HCID 19598128, compound

HRID 274034Notes

Reaction equation

HRID 274034 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]([C:14]2[CH:23]=[CH:22][C:21]3[C:20]([CH3:25])([CH3:24])[CH2:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=3[CH:15]=2)=[O:13])[CH:7]=[CH:6][C:3]=1[CH:4]=O>[Pd].O1CCOCC1>[CH3:24][C:20]1([CH3:25])[CH2:19][CH2:18][C:17]([CH3:26])([CH3:27])[C:16]2[CH:15]=[C:14]([C:12](=[O:13])[CH2:11][O:10][C:8]3[CH:7]=[CH:6][C:3]([CH3:4])=[C:2]([OH:1])[CH:9]=3)[CH:23]=[CH:22][C:21]1=2

Participants

4

Reactant 1

HCID 21474543HCID 21474543, compound

Product 1

HCID 19598128HCID 19598128, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

1 g (2.7 mmol) of 2-hydroxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoylmethyloxy)benzaldehyde, 100 mg of palladium on charcoal (5%) and 50 ml of dioxane are introduced into a reactor. The mixture is hydrogenated at room temperature and under a pressure of 3 bars, the catalyst is filtered off and the filtrate is evaporated. The residue obtained is purified by chromatography on a silica column and eluted with a mixture of hexane and ethyl ether (70:30). After evaporation of the solvents, 600 mg of the expected product, melting point 144°-5° C., are collected.

Workup

  1. customis hydrogenated at room temperature and under a pressure of 3 bars
  2. filtrationthe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customThe residue obtained
  5. customis purified by chromatography on a silica column
  6. washeluted with a mixture of hexane and ethyl ether (70:30)
  7. customAfter evaporation of the solvents, 600 mg of the expected product, melting point 144°-5° C.
  8. customare collected

Sources & evidence

ORD record
ord-90d09efd4018437cbc5f1297d047f9a2
Source dataset
uspto-grants-1995_02
Patent number
US05387594

Reaction notes

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