Hydrochloric Acid → HCID 53950405, compound

HRID 1156181Notes

Reaction equation

HRID 1156181 reaction equation
[Cl-].[CH2:2]([O:4][C:5](=[O:16])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)[CH3:3].[Cl-].[Cl-].[Cl-].[Al+3].Cl.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:2]([O:4][C:5](=[O:16])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:26]1[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=1)=[O:15])[CH3:3]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7964ChlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 86737495HCID 86737495, compound

Product 1

HCID 53950405HCID 53950405, compound

Procedure

Using the method described by Papa et al. [J. Amer.Chem.Soc. 69 (1947), 3018], 12.3 g of azelaic acid ethyl ester chloride in 20 ml of chlorobenzene are mixed cold with 9.5 g of aluminium trichloride and the mixture is then heated at 150° overnight. After adding dilute hydrochloric acid to the complex, the organic phase is washed and concentrated; the residue is extracted with diethyl ether. After column chromatography, and concentration of the solution, 8.3 g of 9-(4-chlorophenyl)-9-oxo-nonanoic acid ethyl ester are obtained as a viscous oil.

Workup

  1. temperaturethe mixture is then heated at 150° overnight
  2. washthe organic phase is washed
  3. concentrationconcentrated
  4. extractionthe residue is extracted with diethyl ether

Sources & evidence

ORD record
ord-212c59a7095e438780e3193e3dfbb1f3
Source dataset
uspto-grants-1982_06
Patent number
US04334089

Reaction notes

Loading…