Acetyl chloride → HCID 5314643, compound

HRID 1465537Notes

Reaction equation

HRID 1465537 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Cl:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([Cl:18])[CH:11]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([Cl:18])[C:11]=1[C:5](=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 365883,5-DichloroanisoleHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5314643HCID 5314643, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of aluminum chloride (4.50 g, 33.9 mmol) and acetyl chloride (2.40 mL, 33.9 mmol) in CH2Cl2 (20.0 mL) was stirred at 0° C. for 30 min. The reaction mixture was slowly added with 1,3-dichloro-5-methoxybenzene (10-1, 2.00 g, 11.3 mmol) in CH2Cl2 (10.0 mL), and the resultant solution was stirred at room temperature for additional 2.0 h. The solution was basified with saturated aqueous NaHCO3. The organic layer was separated, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 1-(2,6-dichloro-4-methoxyphenyl)ethanone (10-2, 1.0 g, 4.6 mmol) as yellow oil in 40% yield: 1H NMR (CDCl3, 500 MHz) δ 7.01 (d, J=1.6 Hz, 2 H), 6.82 (d, J=1.6 Hz, 2 H), 3.83 (s, 3 H), 2.49 (s, 3 H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4(s)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d0841bb61f484397a5283ac7fa2aa824
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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