Acetyl chloride → HCID 20562160, compound

HRID 597267Notes

Reaction equation

HRID 597267 reaction equation
Cl[Sn](Cl)(Cl)Cl.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12][CH:13]=1.[C:20](Cl)(=[O:22])[CH3:21]>C1C=CC=CC=1>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12][C:13]=1[C:20](=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24287Tin tetrachlorideHCID 2579713-Methoxybiphenyl

Product 1

HCID 20562160HCID 20562160, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

52 g of SnCl4 are added dropwise at 5°, while stirring vigorously, to a solution of 36.8 g of 3-methoxy biphenyl and 15.6 g of acetyl chloride in 700 cc of benzene. The mixture is stirred over night at 23°. The reaction mixture is washed twice with 2 N sodium hydroxide and twice with water. Extraction is again effected twice with toluene. The organic phases are combined, dried over anhydrous sodium sulphate and concentrated. 44 g of a crude product are obtained, which are chromatographed on a 20-fold quantity of silica gel. Solvent for absorption and elution: methylene chloride. The crude fractions are crystallized from ether/petroleum ether, whereby 4-acetyl-3-methoxy biphenyl, having an M.P. of 74°-75°, is obtained.

Workup

  1. washThe reaction mixture is washed twice with 2 N sodium hydroxide and twice with water
  2. extractionExtraction
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-638f9ae4f559445d95d8b95e8211a4e1
Source dataset
uspto-grants-1977_03
Patent number
US04013690

Reaction notes

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