Hydrochloric Acid → HCID 14820155, compound

HRID 487074Notes

Reaction equation

HRID 487074 reaction equation
C[O:2][C:3]1[CH:10]=[C:9]([O:11]C)[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[C:13]([C:8]1[C:9]([OH:11])=[CH:10][C:3]([OH:2])=[C:4]([CH:7]=1)[CH:5]=[O:6])(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 691752,4-DimethoxybenzaldehydeHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14820155HCID 14820155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 49.8 g of 2,4-dimethox-ybenzaldehyde, 23.6 ml of acetyl chloride, and 1000 ml of methylene chloride cooled to approximately 0° C. were added 119.7 g of aluminum chloride with stirring under a nitrogen atmosphere. The reaction was allowed to warm to room temperature while stirring overnight. The mixture was added to a slurry of ice and concentrated hydrochloric acid. The organic layer was separated and washed with a saturated sodium chloride solution, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by high pressure liquid chromatography over silica gel eluting with a 0-40% ethyl acetate in hexane gradient. The appropriate fractions were pooled and concentrated to provide 5.85 g of the desired title intermediate, m.p.=142°-143° C.

Workup

  1. temperatureto warm to room temperature
  2. stirringwhile stirring overnight
  3. customThe organic layer was separated
  4. washwashed with a saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by high pressure liquid chromatography over silica gel eluting with a 0-40% ethyl acetate in hexane gradient
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3f3389e51d6a46ebb0578646ae406009
Source dataset
uspto-grants-1994_03
Patent number
US05294613

Reaction notes

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