Hydrochloric Acid → HCID 21154228, compound

HRID 2119232Notes

Reaction equation

HRID 2119232 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:15][CH:16]1[CH2:21][C:20](=[O:22])[O:19][C:17]1=[O:18].[Cl-:23].[Al+3].[Cl-].[Cl-].Cl>O.C(=S)=S>[Cl:23][C:9]1[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=1[C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[C:20](=[O:22])[CH2:21][CH:16]([CH3:15])[C:17]([OH:19])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 163084,4'-DichlorobiphenylHCID 20051Methylsuccinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21154228HCID 21154228, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6348Carbon DisulfideSolvent

Conditions

Temperature
10 °C

Procedure

A solution is prepared by adding 33.4 g dichlorobiphenyl (0.15 moles) and 18.0 g methylsuccinic acid anhydride (0.15 moles) to 100 ml carbon disulfide. The solution is cooled to 10° C. and is treated portionwise, under stirring, with 24.0 g anhydrous aluminum chloride (0.18 moles) at a rate such that the temperature of the reaction mixture does not exceed 15° C. The mixture is stirred for an additional 4 hours at 20° C. and is then decomposed by pouring into a mixture of 350 ml water and 175 ml concentrated hydrochloric acid. Carbon disulfide is distilled off and the residue is washed with 1,2-dichloroethane (2×100 ml and 1×100 ml). The extracts are combined and washed with a 5% aqueous sodium hydroxide solution (5×75 ml) and water (1×75 ml). The alkaline extracts and aqueous washings are combined, filtered with active carbon, and the clear filtrate is acidified to a strong acid with 50% sulfuric acid. The precipitate is separated, washed with water, and purified by crystallization from 95 ml of 65% acetic acid. The yield is 19.3 g (38.0% of theoretical yield) of the title compound with a melting point of 155°-157° C.

Workup

  1. customA solution is prepared
  2. additionis treated portionwise
  3. customdoes not exceed 15° C
  4. distillationCarbon disulfide is distilled off
  5. washthe residue is washed with 1,2-dichloroethane (2×100 ml and 1×100 ml)
  6. washwashed with a 5% aqueous sodium hydroxide solution (5×75 ml) and water (1×75 ml)
  7. filtrationfiltered with active carbon
  8. customThe precipitate is separated
  9. washwashed with water
  10. custompurified by crystallization from 95 ml of 65% acetic acid

Sources & evidence

ORD record
ord-f4888ed967c9486b99ab54f557582501
Source dataset
uspto-grants-1987_07
Patent number
US04683331

Reaction notes

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