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Acetyl chloride → 1-(5-Chloro-2-hydroxy-4-methoxyphenyl)ethanone

HRID 493217
Notes
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Reaction equation

HRID 493217 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[O:10][CH3:11].[Al+3].[Cl-].[Cl-].[Cl-].[C:16](Cl)(=[O:18])[CH3:17]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([O:10][CH3:11])=[CH:4][C:5]([OH:8])=[C:6]([C:16](=[O:18])[CH3:17])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 1389051-Chloro-2,4-dimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 150846361-(5-Chloro-2-hydroxy-4-methoxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Chloro-2,4-dimethoxybenzene (4.94 g, 28.6 mmol) and AlCl3 (4.58 g, 1.2 eq.) were dissolved in 280 ml of CH2Cl2 and cooled down to 0° C. Acetyl chloride (2.03 mL, 1.0 eq.) was slowly added via syringe and the mixture allowed to react for another 3 h at ambient temperature. Pouring onto crashed ice, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by short flash chromatography (SiO2, hexane/AcOEt=95/5), yielded 4.22 g of the title compound as white crystals.

Workup

  1. customto react for another 3 h at ambient temperature
  2. additionPouring
  3. extractionice, twofold extraction with AcOEt
  4. washwashing with water and brine
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-ceb4ae2b22284be39d9bbe204f05c9de
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07534788B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes