Methanol → HCID 67021600, compound

HRID 1661019Notes

Reaction equation

HRID 1661019 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([Cl:16])[C:8]=1[CH2:17][C:18]([OH:20])=[O:19].[CH3:21]O>>[CH3:21][O:19][C:18](=[O:20])[CH2:17][C:8]1[C:7]([Cl:6])=[CH:12][C:11]([N+:13]([O-:15])=[O:14])=[CH:10][C:9]=1[Cl:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22148797HCID 22148797, compound

Product 1

HCID 67021600HCID 67021600, compound

Procedure

Concentrated sulfuric acid (2 mL, 37.33 mmol, 0.73 equiv) is added dropwise to a solution of (2,6-dichloro-4-nitro-phenyl)-acetic acid (EP 87218) (14.2 g, 51.1 mmol) in MeOH (500 mL). The resulting brown solution is stirred for 6 h at reflux. The reaction mixture is allowed to cool to rt and concentrated in vacuo. The residue is dissolved in EtOAc (400 mL) and a bit of water, washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. Purification of the crude product by silica gel column chromatography (Hexane/EtOAc, 2:1→1:1) provides the title compound as a yellow solid: ES-MS: 262.1/264.1 [M+H]+; tR=3.78 min (System 2); Rf=0.40 (Hexane/EtOAc, 2:1).

Workup

  1. temperatureat reflux
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in EtOAc (400 mL)
  4. washa bit of water, washed with a saturated aqueous solution of NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the crude product by silica gel column chromatography (Hexane/EtOAc, 2:1→1:1)

Sources & evidence

ORD record
ord-6fe7c5fedb6f45bda63cc03a62264a16
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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