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

HRID 1606021Notes

Reaction equation

HRID 1606021 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.CCO[CH2:20][CH3:21]>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:21]1[CH:20]=[CH:8][C:7]([Cl:2])=[CH:6][CH:14]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 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 (78.79g, 71.6ml; 0.7mole), AlCl3, (14g, 0.105mole) were mixed, stirred and treated with a solution of 2-hydroxy-3-methylbenzoic acid chloride (12g, 0.07mole) in chlorobenzene (20ml). The mixture was stirred and heated at 100°C overnight. The cooled mixture was added to conc. HCl (10ml) and ice, extraction 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/0.5mm (8.18g), which solidified to yellow microplates, m.p. 55°-58°C.

Workup

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

Sources & evidence

ORD record
ord-0e8f93f33c8b42738192d8c561764468
Source dataset
uspto-grants-1976_04
Patent number
US03951999

Reaction notes

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