Sodium Hydroxide → 4-[3-(4,5,6,7-Tetramethoxyindan-2-yl)propoxy]benzoic acid

HRID 2268486Notes

Reaction equation

HRID 2268486 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[C:8]2[C:4]=1[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=1)[CH2:7]2.[OH-].[Na+]>CO>[CH3:17][O:16][C:9]1[C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:3]([O:2][CH3:1])=[C:4]2[C:8]=1[CH2:7][CH:6]([CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)[CH2:5]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18348584Methyl 4-[3-(4,5,6,7-tetramethoxyindan-2-yl)propoxy]benzoate

Product 1

HCID 183485514-[3-(4,5,6,7-Tetramethoxyindan-2-yl)propoxy]benzoic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-[3-(4,5,6,7-tetramethoxyindan-2-yl)propoxy]benzoate (7.35 g) in methanol (74 ml) was dropwise added aqueous sodium hydroxide (3N, 8.57 ml), which was heated under reflux for 6 hr. The reaction mixture was concentrated in vacuo, made acidic with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was recrystallized from hexane-ethyl acetate to yield the entitled compound (6.58 g) as crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hr
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated aqueous sodium chloride
  6. customdried
  7. customThe solvent was removed in vacuo
  8. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-0176897a26f34b618550289c8aacd1c4
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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