Sulfuric Acid → 7-chloro-1H-isochromen-1-one

HRID 1091426Notes

Reaction equation

HRID 1091426 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH:16]=[CH:17][O:18]C)=[C:11]([CH:15]=1)[C:12]([OH:14])=O>>[Cl:6][C:7]1[CH:15]=[C:11]2[C:10]([CH:16]=[CH:17][O:18][C:12]2=[O:14])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 665936855-Chloro-2-(2-methoxyvinyl)-benzoic acid

Product 1

HCID 116440287-chloro-1H-isochromen-1-oneYield 81%

Procedure

Concentrated sulphuric acid (15 ml) was added to 5-chloro-2(2-methoxyvinyl)-benzoic acid (4.43 g) at 0° C. The mixture was stirred for 2 hours, then diluted with ice/water. The product was extracted with ethyl acetate (3×15 ml) and the combined extracts washed with saturated sodium bicarbonate solution. The solution was dried (magnesium sulfate), filtered and concentrated. The residue was purified by flash chromatography (0-5% ethyl acetate/hexane) to afford the sub-title compound as a white solid (3.04 g, 81%). mp 109.8-110.9° C. 1H NMR (400 MHz, CDCl3) δ 6.51 (1H, d), 7.28-7.32 (1H, m), 7.41 (1H, d), 7.64-7.70 (1H, m), 8.28 (1H, m) ppm.

Workup

  1. extractionThe product was extracted with ethyl acetate (3×15 ml)
  2. washthe combined extracts washed with saturated sodium bicarbonate solution
  3. dry with materialThe solution was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (0-5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-04a3afc30bc645cdb5ee441736cfae66
Source dataset
uspto-grants-2012_03
Patent number
US08129381B2

Reaction notes

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