Benzenemethanol, 3-phenoxy-, 1-acetate → HCID 11447809, compound

HRID 500587Notes

Reaction equation

HRID 500587 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)(=[O:3])[CH3:2]>C(O)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][C:8]=2[CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 170904Benzenemethanol, 3-phenoxy-, 1-acetate

Product 1

HCID 11447809HCID 11447809, compoundYield 15.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-phenoxybenzyl acetate 50 (21.8 g, 90 mmol) (prepared by acetylation of commercial 3-phenoxybenzyl alcohol) and palladium acetate (40 g, 179 mmol) in acetic acid (300 mL) was refluxed for 6 h, cooled and filtered. The filtrate was evaporated to dryness and the residue treated with 100 mL of a mixture cyclohexane/ethyl acetate (6/1) and filtered. The filtrate was concentrated to give a colored oil which was purified by chromatography on silica gel (cyclohexane/ethyl acetate, 6/1) to afford pure dibenzofuran-3-yl-methyl acetate 51 (3.4 g) and a mixture of dibenzofuran-3-yl-methyl acetate 51 (Rf=0.6) and dibenzofuran-1-yl-methyl acetate 52 contaminated with compound 51 (Rf of compound 52=0.53) (8.4 g) as a white solid. 52 will be used without any further purification in the next step

Workup

  1. temperaturewas refluxed for 6 h
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. additionthe residue treated with 100 mL of a mixture cyclohexane/ethyl acetate (6/1)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto give a colored oil which
  9. customwas purified by chromatography on silica gel (cyclohexane/ethyl acetate, 6/1)

Sources & evidence

ORD record
ord-9448c5e759da409babb0a025e7a13e4a
Source dataset
uspto-grants-2010_08
Patent number
US07772237B2

Reaction notes

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