Hydrochloric Acid → HCID 67124134, compound

HRID 871062Notes

Reaction equation

HRID 871062 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl-].[Cl-].[Al+3].ClCC(Cl)(Cl)Cl.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](Cl)=[O:33])=[CH:27][CH:26]=1.Cl>C(Cl)Cl.C1CCCCC1.O>[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][C:4]([C:32](=[O:33])[CH2:31][C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)=[CH:3][CH:2]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7095BiphenylHCID 124181,1,1,2-Tetrachloroethane2×HCID 27346884-Methoxyphenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 67124134HCID 67124134, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

KY-560 In a round bottom flask equipped with gas inlet and magnetic stirrer were placed Biphenyl (2.1 gr, 13.65 mmol), Aluminum trichloride (1.5 gr, 11.25 mmol), and 150 ml of tetrachloroethane (TCM). While the TCM solution was stirring, a solution of 25 ml of tetrachloroethane and 0.830 ml of (4-Methoxy-phenyl)-acetyl chloride (5.5 mmol) was dropwise over five minutes by syringe. The reaction mixture was stirred 3-4 h. 150 ml of water and 5 ml of HCl were slowly added. The layers were separated. The aqueous layer was extracted with DCM. The combined DCM and TCE solution was washed with a saturated solution of NaCl in water. The organic solution was dried over Na2SO4. filtration followed by rotary evaporation produced a dark yellow solid. Chromatography on flash chromatographic (CycloHexane:DCM). Yield 1.2 gr (71%) as a white solid.

Workup

  1. customKY-560 In a round bottom flask equipped with gas inlet and magnetic stirrer
  2. stirringThe reaction mixture was stirred 3-4 h
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted with DCM
  5. washThe combined DCM and TCE solution was washed with a saturated solution of NaCl in water
  6. dry with materialThe organic solution was dried over Na2SO4
  7. filtrationfiltration
  8. customfollowed by rotary evaporation
  9. customproduced a dark yellow solid

Sources & evidence

ORD record
ord-2c42d54b0abe4f228ac19746b9bae9c0
Source dataset
uspto-grants-2015_03
Patent number
US08969573B2

Reaction notes

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