Benzene → 11-Benzoylundecanoic acid

HRID 569108Notes

Reaction equation

HRID 569108 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH2:5]1[C:18](=[O:19])[O:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:18]([OH:17])=[O:19])(=[O:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 6451240Aluminum(III) ChlorideHCID 14098193Oxacyclotridecane-2,13-dione

Product 1

HCID 1223605511-Benzoylundecanoic acid

Procedure

To a stirred suspension of 18 gms AlCl3 (0.135 mole) in 150 ml dry benzene was added 13 gms 1,10-decanedicarboxylic anhydride in small portions over 15 minutes, then the mixture was refluxed for 6 hours. The solid was filtered off, stirred for 2.5 hours in 350 ml 2N HCl, removed by filtration, and stirred in 300 ml 1N NaOH was then heated to 70° and filtered hot. As the solution cooled, solid material (sodium salt of the product) crystallized out. This salt was dissolved in hot water, acidified to pH 3 with concentrated HCl, filtered after cooling, and dried to give 5.5 gm of the desired 11-benzoylundecanoic acid m.p. 83°-6°.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. filtrationThe solid was filtered off
  3. customremoved by filtration
  4. stirringstirred in 300 ml 1N NaOH
  5. temperaturewas then heated to 70°
  6. filtrationfiltered hot
  7. temperatureAs the solution cooled
  8. customsolid material (sodium salt of the product) crystallized out
  9. dissolutionThis salt was dissolved in hot water
  10. filtrationfiltered
  11. temperatureafter cooling
  12. customdried

Sources & evidence

ORD record
ord-2936e3decc9743ee8d244a036979c793
Source dataset
uspto-grants-1988_03
Patent number
US04731382

Reaction notes

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