Methanol → HCID 59224408, compound

HRID 1672440Notes

Reaction equation

HRID 1672440 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][CH:7]2[C:14](N)=[O:15].[OH-:17].[K+].CO>O>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][CH:7]2[C:14]([OH:15])=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 59224415HCID 59224415, compound

Product 1

HCID 59224408HCID 59224408, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 4,5-dimethoxyindane-1-carboxamide (8.4 g, 38.0 mmol), KOH (6.4 g, 114.0 mmol), MeOH (31.0 mL) and water (62 mL) was heated to refluxed for 14 h. The reaction mixture was cooled to room temperature, and MeOH was removed in vacuo. The residue was diluted by 50 mL of water, and the aqueous mixture was extracted with EtOAc (50×2). The aqueous layer was added conc. HCl to adjusted pH ˜1. The solid was filtered, washed by water (100 mL), and dried over P2O5 to afford 4,5-dimethoxyindane-1-carboxylic acid as off-white solid (7.7 g, 92%). M. P.: 128-130° C.

Workup

  1. temperaturewas heated
  2. temperatureto refluxed for 14 h
  3. customMeOH was removed in vacuo
  4. additionThe residue was diluted by 50 mL of water
  5. extractionthe aqueous mixture was extracted with EtOAc (50×2)
  6. additionThe aqueous layer was added conc. HCl to adjusted pH ˜1
  7. filtrationThe solid was filtered
  8. washwashed by water (100 mL)
  9. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-9a13b78547f04752b217ae8a147a4bbb
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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