Hydrochloric Acid → 58457-63-9

HRID 462891Notes

Reaction equation

HRID 462891 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1([CH3:13])[CH2:11][C:10](=[O:12])[O:9][C:7]1=[O:8].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:10]([CH2:11][C:6]([CH3:13])([CH3:5])[C:7]([OH:9])=[O:8])=[O:12])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7964ChlorobenzeneHCID 870672,2-Dimethylsuccinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2028147958457-63-9

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Finely powdered aluminium chloride (29.35 g), 2,2-dimethylsuccinic anhydride (13.9 g) and chlorobenzene (45 ml) were mixed, then stirred and heated on a boiling-water bath for 1.5 hours. The resulting mixture was cooled to room temperature and then poured onto a mixture of ice and water containing a little hydrochloric acid. The resulting mixture was extracted with ether. The ethereal layer was shaken with 2N sodium hydroxide and the resulting aqueous layer washed with ether, acidified with concentrated hydrochloric acid and then extracted with ether. The ethereal layer was washed with water and brine, and finally dried over magnesium sulphate. Removal of the solvent in vacuo gave 13.9 g of 3-(4-chlorobenzoyl)-2,2-dimethylpropionic acid. I.R. (Nujol Mull): 1680 cm-1 (s), 1590 cm-1 (s).

Workup

  1. extractionThe resulting mixture was extracted with ether
  2. stirringThe ethereal layer was shaken with 2N sodium hydroxide
  3. washthe resulting aqueous layer washed with ether
  4. extractionextracted with ether
  5. washThe ethereal layer was washed with water and brine
  6. dry with materialfinally dried over magnesium sulphate
  7. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-55a84516d01447b2b5c5983335c06b3f
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

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