Hydrochloric Acid → (4-Chlorophenyl)(5-ethyl-2-hydroxyphenyl)methanone

HRID 1606014Notes

Reaction equation

HRID 1606014 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:6].[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.Cl>ClC(Cl)C(Cl)Cl>[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](=[O:20])[C:9]2[CH:8]=[C:7]([CH2:5][CH3:6])[CH:12]=[CH:11][C:10]=2[OH:13])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 85014-Chlorobenzoyl chlorideHCID 312424-EthylphenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12562655(4-Chlorophenyl)(5-ethyl-2-hydroxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 65911,1,2,2-TetrachloroethaneSolvent

Conditions

Temperature
105 °C

Procedure

Aluminum chloride (267g) was added in portions over 30 minutes to a stirred solution of 4-ethylphenol (122.1g.) and 4-chloro-benzoyl chloride (140ml.) in dry 1,1,2,2-tetrachloroethane (800ml.). The mixture was heated at 105°C. for 22 hours with stirring, and on cooling a mixture of ice (600g) and concentrated hydrochloric acid was added slowly, A vigorous reaction occurred and some material was lost. The remaining material was separated and the aqueous fraction extracted twice with chloroform (200ml.), and the combined organic layers evaporated to a dark oil which was distilled in vacuo giving two main fractions: B (17.4g) 150°-160°C at 0.3mmHg; C (110.8g) 160°-168°C at 0.3mmHg. Both remained liquid on cooling.

Workup

  1. temperatureon cooling
  2. additionwas added slowly
  3. customA vigorous reaction
  4. customThe remaining material was separated
  5. extractionthe aqueous fraction extracted twice with chloroform (200ml.)
  6. customthe combined organic layers evaporated to a dark oil which
  7. distillationwas distilled in vacuo
  8. customgiving two main fractions
  9. customB (17.4g) 150°-160°C
  10. temperatureBoth remained liquid on cooling

Sources & evidence

ORD record
ord-7e1afd4e3dd344818fb0fc1eba12b8ef
Source dataset
uspto-grants-1976_04
Patent number
US03951999

Reaction notes

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