Methanol → HCID 178458877, compound

HRID 1084665Notes

Reaction equation

HRID 1084665 reaction equation
[C:1]([C:5]1[C:6](=[O:26])[CH2:7][CH:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18]CC3C=CC=CC=3)=[CH:14][CH:13]=2)[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3].C1CCCCC=1.CO.C(Cl)(Cl)Cl>C(OCC)(=O)C.C(O)C.[OH-].[OH-].[Pd+2]>[C:1]([C:5]1[C:6](=[O:26])[CH2:7][CH:8]([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 8079CyclohexeneHCID 178458878HCID 178458878, compound

Product 1

HCID 178458877HCID 178458877, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 21 g (0.060 mol) of 2-propionyl-3-hydroxy-5-(4-benzyloxyphenyl)cyclohex-2-en-1-one in 250 mL of ethyl acetate and 250 mL of absolute ethanol was treated with 12 mL (0.12 mol) of cyclohexene and 0.7 g of 20 percent palladium hydroxide on carbon (Pearlman's catalyst) and the mixture was heated at reflux for 5 hours. The reaction mixture was cooled slightly and filtered through diatomaceous earth. Evaporation of the filtrate from the mixture gave a crude solid residue. Recrystallization of the residue from a 1:1 ethyl acetate-hexane mixture gave the above named product as a beige crystalline solid in a yield of 13.7 g (88 percent of theoretical). The product melted at 135°-137° C.; Rf-0.45 (silica gel, 10:90 MeOH:CHCl3), 1H NMR (CDCl3): δ1.13 (t, 3H, --CH3), 2.55-3.50 (m, 7H, ring protons and --CH 2 CH3), 6.60-7.12 (m, 5H, ArH's and ArOH), 18.15 (broad s, 1H, and enol H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 5 hours
  3. temperatureThe reaction mixture was cooled slightly
  4. filtrationfiltered through diatomaceous earth
  5. customEvaporation of the filtrate from the mixture
  6. customgave a crude solid residue
  7. customRecrystallization of the residue from a 1:1 ethyl acetate-hexane mixture
  8. customgave the

Sources & evidence

ORD record
ord-48bfe27b1e294133a2c789d2cde5807b
Source dataset
uspto-grants-1991_04
Patent number
US05006159

Reaction notes

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