Hydrogen Bromide → (2-Hydroxy-5-methoxyphenyl)(4-hydroxyphenyl)methanone

HRID 429446Notes

Reaction equation

HRID 429446 reaction equation
C(O)C.C([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=2[O:28]C)=[O:19])=[CH:14][CH:13]=1)C1C=CC=CC=1.Br>[Pd].C(O)(=O)C.O.CCOCC>[OH:28][C:21]1[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:20]=1[C:18]([C:15]1[CH:14]=[CH:13][C:12]([OH:11])=[CH:17][CH:16]=1)=[O:19]

Participants

8

Reactant 3

HCID 260Hydrogen BromideHCID 702EthanolHCID 18355592HCID 18355592, compound

Product 1

HCID 15574183(2-Hydroxy-5-methoxyphenyl)(4-hydroxyphenyl)methanone

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

Palladium on carbon catalyst (10%, 1.0 g, 0.94 mmol) was added to a stirred ethanol (500 ml) solution of (4-benzyloxyphenyl)-(2,5-dimethoxyphenyl)-methanone (10.86 g, 31.2 mmol) and the suspension hydrogenated for 18 h. The catalyst was removed by filtration, and the solvent evaporated to give an orange coloured gum. This was dissolved in glacial acetic acid (16 ml), hydrogen bromide (33% w/w in acetic acid, 8.20 ml, 46.76 mmol) added, and the resulting mixture heated to 70° C. for 18 h. The mixture was diluted with water (25ml) and the product extracted into ethyl acetate (3×25 ml). The combined extracts were washed with brine, dried over magnesium sulfate and evaporated to a yellow gum, which was purified by column chromatography on silica gel 60, with 7:3 petrol/ethyl acetate as eluent. This gave a yellow gum, which was dissolved in a minimum of ether and precipitated by adding petrol, to give the title product as a yellow powder.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated
  3. customto give
  4. extractionthe product extracted into ethyl acetate (3×25 ml)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to a yellow gum, which
  8. customwas purified by column chromatography on silica gel 60, with 7:3 petrol/ethyl acetate as eluent
  9. customThis gave a yellow gum, which
  10. customprecipitated
  11. additionby adding petrol

Sources & evidence

ORD record
ord-fd7871611a984ab8af5840aab00f179e
Source dataset
uspto-grants-2001_11
Patent number
US06316494B1

Reaction notes

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