Phenylacetic Acid → 1-(5-Chloro-2,4-dihydroxyphenyl)-2-phenylethan-1-one

HRID 1296861Notes

Reaction equation

HRID 1296861 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([OH:16])=[CH:14][C:13]=1[OH:19]>B(F)(F)F.CCOCC>[Cl:11][C:12]1[C:13]([OH:19])=[CH:14][C:15]([OH:16])=[C:17]([C:8](=[O:10])[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 999Phenylacetic AcidHCID 17314-Chlororesorcinol

Product 1

HCID 589136521-(5-Chloro-2,4-dihydroxyphenyl)-2-phenylethan-1-oneYield 79.3%

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateSolvent

Procedure

This compounds was synthesised in the same manner as described above. Phenylacetic acid (4.71 g, 34.6 mmol), 4-chlororesorcinol (5 g, 34.6 mmol), boron trifloride etherate (30 ml). After standing for two hours an orange precipitate formed. This was purified by flash chromatography to give the required compound as a white solid (7.2 g, 79.3%); Rf 0.9 hexane/ethyl acetate (20/80)].

Workup

  1. customThis compounds was synthesised in the same manner
  2. customan orange precipitate formed
  3. customThis was purified by flash chromatography

Sources & evidence

ORD record
ord-c375ab711bb84f338dc6d5cf1111a416
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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