Acetyl chloride → HCID 21447339, compound

HRID 597265Notes

Reaction equation

HRID 597265 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([O:11][CH3:12])[CH:8]=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3].[C:13](Cl)(=[O:15])[CH3:14].[Sn](Cl)(Cl)(Cl)Cl>C1C=CC=CC=1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:13](=[O:15])[CH3:14])=[C:7]([O:11][CH3:12])[CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24287Tin tetrachlorideHCID 14001754HCID 14001754, compound

Product 1

HCID 21447339HCID 21447339, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

46 g of 3 -isobutyl anisole are added to 500 cc of absolute benzene, and 22 g of acetyl chloride are added. 73 g of tin(IV) chloride are subsequently added dropwise while stirring and cooling at 5°-10°. After stirring at 23° for 16 hours, the reaction mixture is poured on ice, washed once with 2 N hydrochloric acid, twice with a 2 N caustic soda solution and once with water, and the water phases are again extracted twice with benzene. The organic phases are dried over anhydrous sodium sulphate and concentrated. The desired product is obtained in amorphous, pure form from methanol with the careful addition of water. NMR spectrum (CDCl3) inter alia δ=0.9 d (J=6 Hz), 1.3-2.3 m, 2.45 s, 2.55 s, 3.9 s, 6.6-6.9 m, 7.65 d (J=8.6).

Workup

  1. additionare added
  2. temperaturecooling at 5°-10°
  3. stirringAfter stirring at 23° for 16 hours
  4. additionthe reaction mixture is poured on ice
  5. washwashed once with 2 N hydrochloric acid, twice with a 2 N caustic soda solution and once with water
  6. extractionthe water phases are again extracted twice with benzene
  7. dry with materialThe organic phases are dried over anhydrous sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ace4cd8207fe43038206ec7e97a35dd6
Source dataset
uspto-grants-1977_03
Patent number
US04013690

Reaction notes

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