Methanol → HCID 21995897, compound

HRID 1978601Notes

Reaction equation

HRID 1978601 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][C:14]([C:20]([O:22]C)=[O:21])=[CH:13][C:12]=3[CH:24]=2)=[CH:4][CH:3]=1.[OH-].[Na+].CO>C(OCC)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][C:14]([C:20]([OH:22])=[O:21])=[CH:13][C:12]=3[CH:24]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21995797HCID 21995797, compound

Product 1

HCID 21995897HCID 21995897, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To methyl 7-(4-methylphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (1.6 g) was added 1N sodium hydroxide solution (50 ml), methanol (200 ml) and diethylether (100 ml), and the mixture was stirred overnight, concentrated and extracted with water. The aqueous layer was washed with ethyl acetate, made acidic with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated to give 7-(4-methylphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (1.5 g; purity about 70%) as colorless powder.

Workup

  1. concentrationconcentrated
  2. extractionextracted with water
  3. washThe aqueous layer was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7b112e0b519f41e0bc8abb75457e7988
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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