Acetyl chloride → HCID 21447338, compound

HRID 597264Notes

Reaction equation

HRID 597264 reaction equation
[CH:1]1([C:7]2[CH:8]=[C:9]([O:13][CH3:14])[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:15](Cl)(=[O:17])[CH3:16].[Sn](Cl)(Cl)(Cl)Cl>C1C=CC=CC=1>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:15](=[O:17])[CH3:16])=[C:9]([O:13][CH3:14])[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24287Tin tetrachlorideHCID 128783391-Cyclohexyl-3-methoxybenzene

Product 1

HCID 21447338HCID 21447338, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

20 g of 3-cyclohexyl anisole are dissolved in 200 cc of benzene, 8.15 g of acetyl chloride are added, and 27.4 g of tin(IV) chloride are subsequently added dropwise at 5° - 10° while stirring. After stirring at 23° for 16 hours, the reaction mixture is poured on ice and extracted thrice with benzene. The organic phase is successively washed with 2 N hydrochloric acid, a 2 N caustic soda solution and water, is dried over anhydrous sodium sulphate and concentrated. The residue is recrystallized from acetone/petroleum ether. The resulting title compound has a M.P. of 99°-100°.

Workup

  1. stirringAfter stirring at 23° for 16 hours
  2. additionthe reaction mixture is poured on ice
  3. extractionextracted thrice with benzene
  4. washThe organic phase is successively washed with 2 N hydrochloric acid
  5. dry with materiala 2 N caustic soda solution and water, is dried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customThe residue is recrystallized from acetone/petroleum ether

Sources & evidence

ORD record
ord-9f15417109be45ceac00e3ce9eb4edf0
Source dataset
uspto-grants-1977_03
Patent number
US04013690

Reaction notes

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