Hydrochloric Acid → (4-Chlorophenyl)(2-hydroxy-3-methylphenyl)methanone

HRID 1391330Notes

Reaction equation

HRID 1391330 reaction equation
[Al+3].[Cl-:2].[Cl-].[Cl-].[OH:5][C:6]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].Cl>ClC1C=CC=CC=1>[OH:5][C:6]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([C:6]1[CH:14]=[CH:13][C:12]([Cl:2])=[CH:11][CH:7]=1)=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 848312-Hydroxy-3-methylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 223484(4-Chlorophenyl)(2-hydroxy-3-methylphenyl)methanone

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
100 °C

Procedure

Chlorobenzene (78.79 g, 71.6 ml; 0.7 mole) and AlCl3 (14 g, 0.105 mole) were mixed, stirred and treated with a solution of 2-hydroxy-3-methylbenzoic acid chloride (12 g, 0.07 mole) in chlorobenzene (20 ml). The mixture was stirred and heated at 100° C. overnight. The cooled mixture was added to conc. HCl (10 ml) and ice, extracted with ether, and ether washed with saturated sodium bicarbonate solution, dried (Na2SO4), filtered and the filtrate distilled, to give (after removal of the ether), a main fraction 2-hydroxy-3-methyl-4'-chlorobenzophenone, b.p. 148°-152° C./0.5 mm (8.18 g), which solidified to yellow microplates, m.p. 55°-58° C.

Workup

  1. stirringThe mixture was stirred
  2. extractionextracted with ether, and ether
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. distillationthe filtrate distilled
  7. customto give (
  8. customafter removal of the ether), a main fraction 2-hydroxy-3-methyl-4'-chlorobenzophenone, b.p. 148°-152° C./0.5 mm (8.18 g), which

Sources & evidence

ORD record
ord-7d463b3aa04840459cad85e65ea85a4d
Source dataset
uspto-grants-1979_02
Patent number
US04141995

Reaction notes

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