Hydrochloric Acid → 2-(2-Chloro-4-methoxyphenyl)acetic acid

HRID 1602668Notes

Reaction equation

HRID 1602668 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:10](Cl)(=[O:12])[CH3:11].[Cl-].[Al+3].[Cl-].[Cl-].Cl.[OH2:19]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][C:7]=1[CH2:11][C:10]([OH:12])=[O:19]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6367Acetyl chlorideHCID 178333-ChloroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 42091322-(2-Chloro-4-methoxyphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

14.3 g (0.11 mol) of 3-chloroanisole are added at 0° C. to a mixture of 9.3 ml (0.13 mol) of acetyl chloride and 350 ml of methylene chloride. The mixture is stirred for 1 hour and then, with the temperature maintained at 0° C., 24 g (0.18 mol) of aluminum chloride are added and the reaction is allowed to proceed at this temperature for 2 hours. 20 ml of 1 N hydrochloric acid solution and 20 ml of water are then added. The two phases are separated, the organic phase is washed with water, dried over sodium sulfate and filtered and the solvent is evaporated off under reduced pressure. The crude product is purified by chromatography on a silica gel column using an 8/2 cyclohexane/ethyl acetate mixture as the eluent to give the title compound.

Workup

  1. waitto proceed at this temperature for 2 hours
  2. customThe two phases are separated
  3. washthe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe crude product is purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-fc7fe0940f63471db6edd576b67d8f72
Source dataset
uspto-grants-1999_11
Patent number
US05981754

Reaction notes

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