Acetyl chloride → HCID 23434070, compound

HRID 2121710Notes

Reaction equation

HRID 2121710 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH3:8])=[CH:5][C:6]=1[CH3:7].[C:9](Cl)(=[O:11])[CH3:10].[Cl-].[Al+3].[Cl-].[Cl-]>>[C:9]([C:5]1[C:6]([CH3:7])=[C:2]([Cl:1])[S:3][C:4]=1[CH3:8])(=[O:11])[CH3:10]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12875260HCID 12875260, compound

Product 1

HCID 23434070HCID 23434070, compoundYield 73%

Procedure

To a stirred solution of 2-chloro-3,5-dimethylthiophene (0.9 g, 6.18 mmol) in petroleum ether (5 mL) was added acetyl chloride (0.9 mL, 12.4 mmol) and aluminum chloride (0.99 g, 7.42 mmol) at room temperature under nitrogen, and the mixture stirred for 1 day. The reaction mixture was poured into ice water (50 mL) and the whole was extracted with diethyl ether (70 mL×2). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane-ethyl acetate (20:1) to provide the title product (0.85 g, 73% yield).

Workup

  1. extractionthe whole was extracted with diethyl ether (70 mL×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with hexane-ethyl acetate (20:1)

Sources & evidence

ORD record
ord-28102e69cbc145d1a0d3d855e66e18a3
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

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