HCID 54391473, compound → HCID 136076183, compound

HRID 345189Notes

Reaction equation

HRID 345189 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17]CC3C=CC=CC=3)=[CH:13][C:12]=2[O:25][CH3:26])[CH:8]=[C:7]([C:27]([O:29][CH3:30])=[O:28])[N:6]=1)=[O:4]>C(O)C.[Pd]>[CH3:30][O:29][C:27]([C:7]1[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=2[O:25][CH3:26])[CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[N:6]=1)=[O:28]

Participants

4

Reactant 1

HCID 54391473HCID 54391473, compound

Product 1

HCID 136076183HCID 136076183, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 7 g (0.174 mole) of the diester 23 in 200 ml of ethanol was added 1.0 g of 10% Pd/C. The container for the resulting suspension was evacuated and filled with H2 (repeated three times) and kept under a positive atomosphere by means of a hydrogen-filled rubber bladder for 60 hours with very rapid stirring. The mixture was then filtered to remove catalyst and the solvent was removed from the filtrate by rotary evaporation. The resulting oil was dried in vacuo yielding after several hours (4.9 g) 89% of the desired phenol 24 as a solid.

Workup

  1. customThe container for the resulting suspension was evacuated
  2. additionfilled with H2 (repeated three times)
  3. additionfilled rubber bladder for 60 hours with very rapid stirring
  4. filtrationThe mixture was then filtered
  5. customto remove catalyst
  6. customthe solvent was removed from the filtrate by rotary evaporation
  7. customThe resulting oil was dried in vacuo

Sources & evidence

ORD record
ord-293e056845504977a40166a5c1b2f94e
Source dataset
uspto-grants-1991_10
Patent number
US05055578

Reaction notes

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