Sulfuric Acid → HCID 21123734, compound

HRID 2119233Notes

Reaction equation

HRID 2119233 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][CH:6]1[CH2:11][C:10](=[O:12])[O:9][C:7]1=[O:8].[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.S(=O)(=O)(O)O>ClCCCl.Cl>[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:10](=[O:12])[CH2:11][CH:6]([CH3:5])[C:7]([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 20051Methylsuccinic anhydrideHCID 1699742,4-Difluoro-1,1'-biphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21123734HCID 21123734, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
15 °C

Procedure

A solution is prepared by dissolving 33.2 g anhydrous aluminum chloride (0.25 moles) and 21.6 g methylsuccinic acid anhydride (0.188 moles) in 190 ml of 1,2-dichloroethane. The solution is cooled to 15° C. and is treated under stirring and cooling with a solution of 47.5 g of 2,4-difluorobiphenyl (0.25 moles) in 50 ml of 1,2-dichloroethane, at a rate such that the temperature of the reaction mixture does not exceed 20° C. The mixture is then stirred for an additional 3 hours at 20° C., for 1 hour at 40° to 45° C., is cooled to 20° C., and is then poured slowly, under stirring, into a mixture of 500 g ice in 250 ml of concentrated hydrochloric acid. The resulting precipitate is collected on a filter, and the organic layer of the filtrate is separated and washed with 5% aqueous sodium hydroxide solution (4×100 ml). The alkaline extracts are combined and the precipitate is dissolved in the extracts. A moderately turbid solution is obtained, which is filtered with active carbon to obtain a clear filtrate. The clear filtrate is acidified to approximately pH 1 with 50% sulfuric acid. The crude product precipitate is separated, washed with water, and purified by crystalization from 160 ml of 65% acetic acid, to yield 24.0 g of the title compound (42% of theoretical yield) with a melting point of 150°-152° C.

Workup

  1. customA solution is prepared
  2. additionis treated
  3. customdoes not exceed 20° C
  4. stirringThe mixture is then stirred for an additional 3 hours at 20° C., for 1 hour at 40° to 45° C.
  5. temperatureis cooled to 20° C.
  6. additionis then poured slowly
  7. customThe resulting precipitate is collected on a filter
  8. customthe organic layer of the filtrate is separated
  9. washwashed with 5% aqueous sodium hydroxide solution (4×100 ml)
  10. dissolutionthe precipitate is dissolved in the extracts
  11. customA moderately turbid solution is obtained
  12. filtrationwhich is filtered with active carbon
  13. customto obtain a clear filtrate
  14. customThe crude product precipitate is separated
  15. washwashed with water
  16. custompurified by crystalization from 160 ml of 65% acetic acid

Sources & evidence

ORD record
ord-d0774d9bf3da4b45961ad015d5671481
Source dataset
uspto-grants-1987_07
Patent number
US04683331

Reaction notes

Loading…