Hydrochloric Acid → 2,4-Dihydroxy-phenyl-benzyl-ketone

HRID 2254357Notes

Reaction equation

HRID 2254357 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:13]1([CH2:19][C:20](Cl)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>ClC(Cl)C>[OH:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=1[CH:19]([C:20]([CH:19]([C:6]1[CH:7]=[CH:8][C:1]([OH:2])=[CH:3][C:4]=1[OH:5])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 7679Phenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 540149872,4-Dihydroxy-phenyl-benzyl-ketoneYield 90.9%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

55 g (0.5 mole) of resorcinol were suspended in 250 ml of dichloro ethane and at 20° C. 67 g (0.502 mole) of anhydrous aluminum chloride were added. To the obtained homogeneous dark solution, containing the hydrogen-aluminum-trichloro-3-hydroxy-phenolate, 77.2 g (0.5 mole) of phenyl-acetyl chloride in 100 ml of dichloro ethane were added over one hour while the temperature raised to 35°-40° C. The reaction mixture was stirred for one hour, the solution thus obtained was added to an aqueous hydrochloric acid solution, the two layers were separated, the organic layer was washed with water to neutral, the solvent was distilled off and the residue was optionally crystallized from toluene. 96.9 g of 2,4-dihydroxy-phenyl-benzyl-ketone were obtained, m.p.: 112°-114° C., yield: 85%. After an optional recrystallization from toluene the melting point was 113°-114° C. Elemental analysis for C14H12O3 (Mw: 228):

Workup

  1. additionwere added over one hour while the temperature
  2. temperatureraised to 35°-40° C
  3. customthe solution thus obtained
  4. customthe two layers were separated
  5. washthe organic layer was washed with water to neutral, the solvent
  6. distillationwas distilled off
  7. customthe residue was optionally crystallized from toluene

Sources & evidence

ORD record
ord-a0581d028d0944308c3273f2b5c7db8d
Source dataset
uspto-grants-1993_08
Patent number
US05235109

Reaction notes

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