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

HRID 1391328Notes

Reaction equation

HRID 1391328 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

Aluminium chloride (267 g) was added in portions over 30 minutes to a stirred solution of 4-ethylphenol (122.1 g.) and 4-chlorobenzoyl chloride (140 ml.) in dry 1,1,2,2-tetrachloroethane (800 ml.). The mixture was heated at 105° C. for 22 hours with stirring, and on cooling a mixture of ice (600 g) and concentrated hydrochloric acid was added slowly. A vigorous reaction occurred and some material was lost. The remaining material was separated, the aqueous fraction extracted twice with chloroform (200 ml.), and the combined organic layers evaporated to a dark oil which was distilled in vacuo giving two main fractions: B (17.4 g) 150°-160° C. at 0.3 mmHg; C (110.8 g) 160°-168° C. at 0.3 mmHg. The title compound was crystallised by cooling to -20° C. and recrystallised from n-hexane at 0° C. to give a yellow crystalline solid m.p. 35°-8° C.

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 (200 ml.)
  6. customthe combined organic layers evaporated to a dark oil which
  7. distillationwas distilled in vacuo
  8. customgiving two main fractions
  9. customB (17.4 g) 150°-160° C.
  10. customC (110.8 g) 160°-168° C.
  11. customThe title compound was crystallised
  12. temperatureby cooling to -20° C.
  13. customrecrystallised from n-hexane at 0° C.

Sources & evidence

ORD record
ord-24f31516e4db42cf9af6f18d87063f3e
Source dataset
uspto-grants-1979_02
Patent number
US04141995

Reaction notes

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