Acetyl chloride → HCID 69880513, compound

HRID 1838038Notes

Reaction equation

HRID 1838038 reaction equation
ClC1C=[C:6]([C:7](O)=[O:8])C(C(O)=O)=C(Cl)C=1C(O)=O.[Cl:18][C:19]1([CH3:27])[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]1[CH3:26].[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)(=O)C>>[C:7]([C:21]1[CH:20]([CH3:26])[C:19]([Cl:18])([CH3:27])[CH:24]=[CH:23][C:22]=1[Cl:25])(=[O:8])[CH3:6]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 22222868HCID 22222868, compoundHCID 68565778HCID 68565778, compound

Product 1

HCID 69880513HCID 69880513, compound

Procedure

Synthesis of dichlorotrimellitic acid—The reaction scheme for this synthesis is depicted in FIG. 7. Into a 250 ml round bottom flask was put 2,5-dichloroxylene (5 g, 28.6 mmol) and aluminum chloride (4.6 g, 34.3 mmol). Solids were thoroughly mixed, then acetyl chloride (2.0 mL, 28.6 mmol) was added and the reaction immersed in an oil bath at 70° C. After cessation of gas evolution (approx 30 min), reaction was allowed to cool to room temperature and partitioned between ethyl acetate (100 mL) and water (200 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to yield 5 g of 6-acetyl-2,5-dichloroxylene as a yellow oil. This crude was used directly for the subsequent oxidation without purification.

Workup

  1. customThe reaction scheme for this synthesis
  2. customInto a 250 ml round bottom flask was put
  3. additionSolids were thoroughly mixed
  4. customthe reaction immersed in an oil bath at 70° C
  5. customAfter cessation of gas evolution (approx 30 min), reaction
  6. custompartitioned between ethyl acetate (100 mL) and water (200 mL)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75327001c8474a55a1deb461e109f04e
Source dataset
uspto-grants-2004_01
Patent number
US06673550B2

Reaction notes

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