HCID 57421333, compound → HCID 19361971, compound

HRID 1457164Notes

Reaction equation

HRID 1457164 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9]C)[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([O:14]C)=[O:13]>Br.O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=[O:13]

Participants

4

Reactant 1

HCID 57421333HCID 57421333, compound

Product 1

HCID 19361971HCID 19361971, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

2,3-Dichloro-4-methoxybenzeneacetic acid, methyl ester, 46 gm, was refluxed for 18 hours in concentrated HBr, 350 mL. The reaction mixture was poured in water, 1.4 L, and the solution was extracted with EtOAc, 2×500 mL. The organic layers were washed with water, dried (Na2SO4) and concentrated to dryness. The residue was slurried in 20% EtOAc-hexane to yield 2,3-dichloro-4-hydroxybenzeneacetic acid, mp 189°-190° C. The acid was stirred at room temperature in methanolic HCl, 100 mL, for 30 minutes. The volatiles were removed in vacuo and the residue was slurried in hexane, filtered and air-dried to yield 17.6 gm of the title compound, mp 105°-106° C., analysis, calculated: C, 45.98; H, 3.43; Cl, 30.16; obtained: C, 46.10; H, 3.65; Cl, 30.31.

Workup

  1. extraction1.4 L, and the solution was extracted with EtOAc, 2×500 mL
  2. washThe organic layers were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d63bf427dcc543678a29095e5d5a0c76
Source dataset
uspto-grants-1998_12
Patent number
US05847008

Reaction notes

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