Resorcinol → 2-(4-Chlorophenyl)-1-(2,4-dihydroxyphenyl)ethanone

HRID 14494

Reaction equation

HRID 14494 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17](O)=[O:18])=[CH:12][CH:11]=1.B(F)(F)F.CCOCC.C([O-])(=O)C.[Na+]>>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([C:6]2[CH:7]=[CH:8][C:1]([OH:2])=[CH:3][C:4]=2[OH:5])=[O:18])=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 5054ResorcinolHCID 8000Boron trifluoride etherateHCID 15880(4-Chlorophenyl)acetic acidHCID 517045Sodium Acetate

Product 1

HCID 5863662-(4-Chlorophenyl)-1-(2,4-dihydroxyphenyl)ethanone

Conditions

Temperature
85 °C

Procedure

A mixture of resorcinol (100 g, 0.908 mol), 4-chlorophenylacetic acid (170 g, 0.999 mol) and boron trifluoride etherate is stirred mechanically at 85° C. for 1.75 h. The dark red-brown reaction mixture is allowed to cool to room temperature and then poured slowly into aqueous sodium acetate (1 l, 30% w/v). The suspension is stirred overnight at room temperature. The orange brown precipitate is removed by filtration, dried in vacuo and then triturated with isopropyl ether/hexane (1:9) to give a yellow solid. This solid is washed with hexane and dried in vacuo to provide the title compound. A further three crops of material are obtained from the sodium acetate work-up mixture.

Workup

  1. temperatureto cool to room temperature
  2. stirringThe suspension is stirred overnight at room temperature
  3. customThe orange brown precipitate is removed by filtration
  4. customdried in vacuo
  5. customtriturated with isopropyl ether/hexane (1:9)
  6. customto give a yellow solid
  7. washThis solid is washed with hexane
  8. customdried in vacuo

Sources & evidence

ORD record
ord-a542f2d9ff694a16a34c015a0ccdb19f
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Linked notes

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