Methanol → HCID 22387885, compound

HRID 1072816Notes

Reaction equation

HRID 1072816 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[C:4]([C:6]1[C:7]2[CH:15]=[C:14]([C:16]([O:18]C)=[O:17])[CH:13]=[CH:12][C:8]=2[O:9][C:10]=1[CH3:11])=O.CO.[OH-].[Na+]>O1CCCC1>[C:16]([C:14]1[CH:13]=[CH:12][C:8]2[O:9][C:10]([CH3:11])=[C:6]([CH2:4][C:3]3[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:2]=3[Cl:1])[C:7]=2[CH:15]=1)([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22388405HCID 22388405, compound

Product 1

HCID 22387885HCID 22387885, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(2,4-dichlorobenzoyl)-5-(methoxycarbonyl)-2-methylbenzo[b]furan (0.57 g, 1.6 mmol), methanol (6 ml), tetrahydrofuran (6 ml) and a 2M aqueous sodium hydroxide solution (8.5 ml) was refluxed under heating for 40 min. The reaction mixture was concentrated under reduced pressure and water was added to the residue. The mixture was acidified with 3N hydrochloric acid and the precipitated solid was extracted with hot ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure to give the objective compound (0.54 g, quantitative) as colorless crystals.

Workup

  1. temperatureunder heating for 40 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure and water
  3. additionwas added to the residue
  4. extractionthe precipitated solid was extracted with hot ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe desiccant was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customto give the objective compound (0.54 g, quantitative) as colorless crystals

Sources & evidence

ORD record
ord-a036cf9fb5334e309c1f62ab1eeb10eb
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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