Water → 4-Methoxy-3-isochromanone

HRID 617399Notes

Reaction equation

HRID 617399 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH3:18][O:19][CH:20]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][O:33][CH:34]1CCCC[O:35]1)C(OCC)=O.O>CO>[CH3:18][O:19][CH:20]1[C:26]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:32][O:33][C:34]1=[O:35]

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 18357803Ethyl alpha-methoxy-2-(tetrahydropyran-2-yloxymethyl)phenylacetate

Product 1

HCID 155472854-Methoxy-3-isochromanoneYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridinium p-toluenesulfonate (0.30 g) was added to a solution of ethyl α-methoxy-2-(tetrahydropyran-2-yloxy-methyl)phenylacetate (14.00 g, 45.4 mmol) in methanol (50 ml), and the mixture was heated under reflux for 1 hour. The mixture was cooled to room temperature, and water (50 ml) was added. The mixture was extracted with methylene chloride and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by recrystallization from n-hexane/ethyl acetate (=1/1) to give the desired compound 4-methoxy-3-isochromanone (6.00 g, 74.2%) as white crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. extractionThe mixture was extracted with methylene chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by recrystallization from n-hexane/ethyl acetate (=1/1)

Sources & evidence

ORD record
ord-5f8fd03e8b974d4cb63bfdc7c3fcf2fc
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

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