Hydrochloric Acid → (2-Hydroxy-4,6-dimethylphenyl)(2-methylphenyl)methanone

HRID 1395054Notes

Reaction equation

HRID 1395054 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C1(C)C(C([O:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=2)=O)=CC=CC=1.O.Cl.C([O:27][CH2:28][CH3:29])C>>[OH:13][C:14]1[CH:15]=[C:16]([CH3:21])[CH:17]=[C:18]([CH3:20])[C:19]=1[C:28]([C:29]1[CH:18]=[CH:19][CH:14]=[CH:15][C:16]=1[CH3:17])=[O:27]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 532243o-Toluic acid, 3,5-dimethylphenyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20341544(2-Hydroxy-4,6-dimethylphenyl)(2-methylphenyl)methanone

Procedure

Anhydrous aluminum chloride (20 g.) was added in portions during 5 minutes to 3,5-dimethylphenyl o-toluate (36.3 g.) and the mixture was heated at 140°-150° C. for 3 hours. After cooling, water (300 ml.) and concentrated hydrochloric acid (25 ml.) were added and the mixture was stirred and heated on the steam-bath until hydrolysis was complete. After cooling, the mixture was stirred with diethyl ether (110 ml.) and filtered through charcoal and kieselguhr. The layers were separated and the aqueous phase was extracted with more diethyl ether (2×50 ml.). The combined ethereal solutions were washed with water, dried over sodium sulphate and evaporated in vacuo. The residue crystallised slowly. Light petroleum (b.p. 40°-60° C.; 50 ml.) was added and the solid was filtered off, washed with light petroleum (b.p. 40°-60° C.) at 0° C. and dried in a vacuum desiccator. The solid was recrystallised from methanol to give 2-hydroxy-2',4,6-trimethylbenzophenone (15.9 g.), m.p. 65° -67° C.

Workup

  1. temperaturethe mixture was heated at 140°-150° C. for 3 hours
  2. temperatureAfter cooling
  3. temperatureheated on the steam-bath until hydrolysis
  4. temperatureAfter cooling
  5. filtrationfiltered through charcoal and kieselguhr
  6. customThe layers were separated
  7. extractionthe aqueous phase was extracted with more diethyl ether (2×50 ml.)
  8. washThe combined ethereal solutions were washed with water
  9. dry with materialdried over sodium sulphate
  10. customevaporated in vacuo
  11. customThe residue crystallised slowly
  12. additionLight petroleum (b.p. 40°-60° C.; 50 ml.) was added
  13. filtrationthe solid was filtered off
  14. washwashed with light petroleum (b.p. 40°-60° C.) at 0° C.
  15. customdried in a vacuum desiccator
  16. customThe solid was recrystallised from methanol

Sources & evidence

ORD record
ord-92350359fcc9407b9f3d8181fb0bfec6
Source dataset
uspto-grants-1980_05
Patent number
US04201790

Reaction notes

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