Methanol → 6-chloro-4-phenylisocoumarin-3-carboxylic Acid Methyl Ester

HRID 750113Notes

Reaction equation

HRID 750113 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[C:8](=[O:9])[O:7][C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.S(=O)(=O)(O)O.[CH3:27]O>>[CH3:27][O:14][C:13]([C:6]1[O:7][C:8]([C:10]2[C:4]([C:5]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:3][C:2]([Cl:1])=[CH:12][CH:11]=2)=[O:9])=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 103800926-chloro-4-phenylisocoumarin-3-carboxylic Acid

Product 1

HCID 691565656-chloro-4-phenylisocoumarin-3-carboxylic Acid Methyl Ester

Procedure

To a solution of 6-chloro-4-phenylisocoumarin-3-carboxylic acid (9 g) in methanol (200 ml) was added sulfuric acid (20 ml) and the mixture was refluxed for 2 hrs. The reaction mixture was concentrated, and the residue was neutralized with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated. The residue was crystallized from isopropyl ether to give the title compound (8.7 g) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 2 hrs
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-1f6c20759aa44496aed9d6e5f123b6c8
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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