Hydrochloric Acid → 2-(2-Chlorophenyl)propanoic acid

HRID 547450Notes

Reaction equation

HRID 547450 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[Li+].[CH3:13]C([N-]C(C)C)C.CCCCCCC.C(C1C=CC=CC=1)C.CI.Cl>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:13])[C:9]([OH:11])=[O:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 7500EthylbenzeneHCID 17124o-Chlorophenylacetic acidHCID 86599834LDA heptane

Product 1

HCID 126365742-(2-Chlorophenyl)propanoic acidYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

To 1 g of 2-chlorophenylacetic acid, 8.8 mL of 2M LDA heptane, THF, ethylbenzene solution was dropped under cooling with ice, and further 1.58 g of HMPA and 5 mL of THF were added followed by an hour's stirring at room temperature. Then 1.25 g of methyl iodide was added under cooling with ice and stirred at room temperature for 30 minutes. The reaction solution was poured into ice water, rendered acidic with 10% aqueous hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was dried over anhydrous magnesium sulfate and thereafter removed of the solvent by distillation under reduced pressure. The residue was purified on 30 g silica gel column chromatography (eluent, chloroform:methanol=20:1) to provide 0.928 g (yield: 86%) of the title compound as a pale yellow, oily substance.

Workup

  1. additionwere added
  2. waitfollowed by an hour
  3. temperatureunder cooling with ice
  4. stirringstirred at room temperature for 30 minutes
  5. extractionextracted with ethyl acetate
  6. extractionThe ethyl acetate extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. customremoved of the solvent by distillation under reduced pressure
  9. customThe residue was purified on 30 g silica gel column chromatography (eluent, chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-3516f7351d9c490d96e9f8e8bf1a4c85
Source dataset
uspto-grants-2011_05
Patent number
US07939536B2

Reaction notes

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