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

HRID 2254359Notes

Reaction equation

HRID 2254359 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.O>[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

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 5054ResorcinolHCID 7679Phenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 540149872,4-Dihydroxy-phenyl-benzyl-ketoneYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

120 kg (1.09 kmole) of resorcinol were suspended in 660 l of dichlorethane and 150 kg (1.12 kmole) of anhydrous aluminum chloride were added to the suspension while the temperature raised from 15° C. to 25° C. The complex obtained dissolved in the reaction medium. 171 kg (1.10 kmole) of phenyl-acetyl chloride were added over a period of one hour while the temperature raised to 35°-40° C. The mixture was stirred for one hour thereafter it was admixed with diluted hydrogen chloride (the mixture of 300 l of hydrogen chloride and 600 l of water), and it was treated as described in the preceding Examples. The solvent was removed by distillation, the residue was recrytallized from toluene, the product obtained was centrifuged and dried at 45°-50° C. 205-210 kg of 2,4-dihydroxy-phenyl-benzyl-ketone were obtained, yield 82-84.5%. Calculated amount: 248.5 kg. The physical data are identical with the data given in Example 1.

Workup

  1. temperatureraised from 15° C. to 25° C
  2. customThe complex obtained
  3. dissolutiondissolved in the reaction medium
  4. temperatureraised to 35°-40° C
  5. additionwas treated
  6. customThe solvent was removed by distillation
  7. customthe product obtained
  8. customdried at 45°-50° C

Sources & evidence

ORD record
ord-bcc321d4f7a3489b9a3b95da51a2e52d
Source dataset
uspto-grants-1993_08
Patent number
US05235109

Reaction notes

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