HCID 19748023, compound → HCID 9863987, compound

HRID 654221Notes

Reaction equation

HRID 654221 reaction equation
[CH3:1][C:2]1[C:3]([C:16]([O:18][C:19]2[CH:34]=[CH:33][C:22]([C:23]([O:25]CC3C=CC=CC=3)=[O:24])=[CH:21][CH:20]=2)=[O:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1>[Pd].C(OCC)(=O)C>[CH3:1][C:2]1[C:3]([C:16]([O:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:33][CH:34]=2)=[O:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

4

Reactant 1

HCID 19748023HCID 19748023, compound

Product 1

HCID 9863987HCID 9863987, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 430 mg (0.94 mmol) of benzyl 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate, 60 mg of 10% palladium on carbon and 6 ml of ethyl acetate was stirred under a hydrogen atmosphere at room temperature for 3 hours. A further 6 ml of ethyl acetate was then added to the reaction mixture and mixture heated at 50° C. for 3 hours. The reaction mixture was then cooled, filtered through celite and the residue washed with 5 ml of warm ethyl acetate. The filtrate was then concentrated in-vacuo and the resultant residue recrystallized from a mixture of ethyl acetate and hexanes to give the title compound as a white, crystalline solid.

Workup

  1. temperatureheated at 50° C. for 3 hours
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered through celite
  4. washthe residue washed with 5 ml of warm ethyl acetate
  5. concentrationThe filtrate was then concentrated in-vacuo
  6. customthe resultant residue recrystallized from a mixture of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-f9a3a32eeebc4ba38609492e4757787f
Source dataset
uspto-grants-1992_07
Patent number
US05130335

Reaction notes

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