Hydrochloric Acid → 1-(4-Chloro-2-hydroxy-5-methoxy-phenyl)-ethanone

HRID 38376Notes

Reaction equation

HRID 38376 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Cl:9][C:10]1[CH:15]=[C:14]([O:16]C)[CH:13]=[CH:12][C:11]=1[O:18][CH3:19].Cl>C(Cl)Cl>[Cl:9][C:10]1[C:11]([O:18][CH3:19])=[CH:12][C:13]([C:5](=[O:7])[CH3:6])=[C:14]([OH:16])[CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 2467242-Chloro-1,4-dimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 595985801-(4-Chloro-2-hydroxy-5-methoxy-phenyl)-ethanoneYield 527.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of AlCl3 (8.89 g, 59 mmol) in CH2Cl2 at −10° C. was added acetyl chloride (4.1 ml, 58 mmol) drop-wise while maintaining the internal temperature below 0° C. After 20 min 2-Chloro-1,4-dimethoxybenzene (10.0 g, 8.3 mmol) was dissolved in 8 ml CH2Cl2 and added to the above solution drop-wise while maintaining the internal temperature below 0° C. After 20 min the mixture was warmed to room temperature for 1 hour then warmed to reflux. After 21 h the solution was cooled, poured over a mixture of ice and concentrated HCl and extracted with dichloromethane. The combined organics were concentrated in vacuo and recrystallized from H2O/EtOH to afford 1-(4-chloro-2-hydroxy-5-methoxy-phenyl)-ethanone (8.78 g, 85%) as a solid.

Workup

  1. temperaturewhile maintaining the internal temperature below 0° C
  2. additionadded to the above solution drop-wise
  3. temperaturewhile maintaining the internal temperature below 0° C
  4. temperaturethen warmed to reflux
  5. temperatureAfter 21 h the solution was cooled
  6. extractionextracted with dichloromethane
  7. concentrationThe combined organics were concentrated in vacuo
  8. customrecrystallized from H2O/EtOH

Sources & evidence

ORD record
ord-27836df41ecf407fae7b9f15300f9b41
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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