Hydrochloric Acid → HCID 67402766, compound

HRID 852383Notes

Reaction equation

HRID 852383 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([C:12]([O:14][CH2:15]C)=[O:13])([CH3:11])[CH3:10])[C:5]([Cl:17])=[CH:4][C:3]=1[O:18]C(=O)C1C=CC=CC=1.[Na].Cl>CO>[CH3:15][O:14][C:12](=[O:13])[C:9]([O:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([OH:18])=[CH:4][C:5]=1[Cl:17])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 86601451HCID 86601451, compound

Product 1

HCID 67402766HCID 67402766, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To an ice cold solution of 500 mg (1.3 mmol) benzoic acid 2,5-dichloro-4-(1-ethoxycarbonyl-1-methyl-ethoxy)-phenyl ester in 11.5 ml methanol was added a solution of 145 mg (6.3 mmol) sodium in 11.5 ml methanol within 5 min under an argon atmosphere. The solution was stirred for 4 h at ambient temperature, cooled to 0° C. and carefully neutralized with 1 N HCl. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and brine/ice water 1/1. The layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed with brine/ice water 1/1 and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, heptane/AcOEt) to give 219 mg (0.8 mmol, 62%) of the title compound as colorless oil.

Workup

  1. temperaturecooled to 0° C.
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted two times with ethyl acetate
  6. washThe combined organic layers were washed with brine/ice water 1/1
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue purified by column chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-c0afa411ea8041719a7ebfd26e92c86e
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

Loading…