Hydrochloric Acid → 2-(2-Methylphenoxymethyl)-phenylacetic acid methyl ester

HRID 726853Notes

Reaction equation

HRID 726853 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH3:15][O:16][C:17](=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25]Br.Cl>C(#N)C>[CH3:15][O:16][C:17](=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][O:7][C:6]1[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=1[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 335O-CresolHCID 11430Potassium CarbonateHCID 15168495Benzeneacetic acid, 2-(bromomethyl)-, methyl ester

Product 1

HCID 536881362-(2-Methylphenoxymethyl)-phenylacetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

5.12 g of o-cresol and 7.2. g of pulverized potash in 30 ml of acetonitrile are preheated to 60° C. and a solution of 11.06 g of 2-(bromomethyl)-phenylacetic acid methyl ester in 35 ml of acetonitrile is added dropwise over a period of 8 minutes. The reaction mixture is then stirred for 4 minutes and immediately poured onto ice-water and weakly acidified with 2N hydrochloric acid. The aqueous solution is extracted exhaustively with ethyl acetate and the combined organic phases are washed with water, dried over sodium sulfate, filtered and concentrated by evaporation. Chromatography on silica gel with hexane/ethyl acetate (9:1) yields pure 2-(2-methylphenoxymethyl)-phenylacetic acid methyl ester in the form of a pale yellow oil.

Workup

  1. customare preheated to 60° C.
  2. additionimmediately poured onto ice-water
  3. extractionThe aqueous solution is extracted exhaustively with ethyl acetate
  4. washthe combined organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2870eb0d1b2b499d9a5282426bf24868
Source dataset
uspto-grants-1998_01
Patent number
US05710314

Reaction notes

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