1,5-Bis(4-hydroxyphenyl)-1,4-pentadien-3-one → 3-Pentanone, 1,5-bis(4-hydroxyphenyl)-

HRID 979068Notes

Reaction equation

HRID 979068 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:20])[CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1>C(O)(=O)C.[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:20])[CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 1074411,5-Bis(4-hydroxyphenyl)-1,4-pentadien-3-one

Product 1

HCID 107071713-Pentanone, 1,5-bis(4-hydroxyphenyl)-Yield 88.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 20 g (0.075 mol) of 1,5-bis(4-hydroxyphenyl)penta 1,4-diene-3-one of Example 16 in 200 ml of glacial acetic acid and 1.5 g of 5% Pd/C was placed on a Parr hydrogenator for 2 hours under hydrogen. This reaction was repeated and the two solutions were filtered and evaporated to give a viscous oil (18 g). This was chromotographed on a silica gel column (Woelm) and eluted with CHCl3 :MeOH (95:5). The product (7.0 g) was recovered first and then 9.0 g of the corresponding alcohol.

Workup

  1. filtrationthe two solutions were filtered
  2. customevaporated

Sources & evidence

ORD record
ord-0579b897c09b43bc96451f3d7ecdc106
Source dataset
uspto-grants-1987_05
Patent number
US04666909

Reaction notes

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