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

HRID 655819Notes

Reaction equation

HRID 655819 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).

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-d421f84f376b42179d98a38b90a6619d
Source dataset
uspto-grants-2011_12
Patent number
US08071618B2

Reaction notes

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