1,4-Dioxane → 4,5-Dichloro-2-formylbenzoic acid

HRID 655832Notes

Reaction equation

HRID 655832 reaction equation
Br[CH:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:12])=[C:8]([Cl:11])[CH:9]=2)[C:4](=[O:13])[O:3]1.[O:14]1CCOCC1>Cl>[Cl:11][C:8]1[C:7]([Cl:12])=[CH:6][C:5]([C:4]([OH:3])=[O:13])=[C:10]([CH:2]=[O:14])[CH:9]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 144180783-Bromo-5,6-dichloro-3H-isobenzofuran-1-one

Product 1

HCID 865917864,5-Dichloro-2-formylbenzoic acidYield 73%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 3-bromo-5,6-dichloro-3H-isobenzofuran-1-one (2.0 g) in 5% aqueous HCl (10 mL) and 80% aqueous dioxane (25 mL) were heated to reflux for 2 hours. The solvent was removed and the resulting residue re-dissolved in ethyl acetate, dried (magnesium sulfate) and concentrated. The resultant yellow solid was recrystallized from DCM/hexane to give the sub-title compound as a white solid (1.13 g, 73%); 1H NMR (400 MHz, CDCl3) δ 6.66 (0.84H, s), 7.95 (0.16H, s), 8.05 (0.84H), 8.12 (0.16H, s), 8.14 (0.84H, s), 8.41 (0.84H,), 10.41 (0.16H, s), 11.07 (0.16 H, brs).

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was removed
  4. dissolutionthe resulting residue re-dissolved in ethyl acetate
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated
  7. customThe resultant yellow solid was recrystallized from DCM/hexane

Sources & evidence

ORD record
ord-f916b648223b46d4977b6c22571511b6
Source dataset
uspto-grants-2011_12
Patent number
US08071618B2

Reaction notes

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