Sodium Hydroxide → 2-(8-Hydroxyoctyl)-4,5,6,7-tetramethoxy-2-indancarboxylic acid

HRID 2268449Notes

Reaction equation

HRID 2268449 reaction equation
[OH-].[Na+].[OH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1([C:29]([O:31]CC)=[O:30])[CH2:20][C:19]2[C:14](=[C:15]([O:27][CH3:28])[C:16]([O:25][CH3:26])=[C:17]([O:23][CH3:24])[C:18]=2[O:21][CH3:22])[CH2:13]1>C(O)C>[OH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1([C:29]([OH:31])=[O:30])[CH2:20][C:19]2[C:14](=[C:15]([O:27][CH3:28])[C:16]([O:25][CH3:26])=[C:17]([O:23][CH3:24])[C:18]=2[O:21][CH3:22])[CH2:13]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18348653Ethyl 2-(8-hydroxyoctyl)-4,5,6,7-tetramethoxy-2-indancarboxylate

Product 1

HCID 183485542-(8-Hydroxyoctyl)-4,5,6,7-tetramethoxy-2-indancarboxylic acidYield 50.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous sodium hydroxide solution (3N, 1.07 ml, 3.22 mmols) was added to an ethanol (10 ml) solution of ethyl 2-(8-hydroxyoctyl)-4,5,6,7-tetramethoxy-2-indancarboxylate (708 mg, 1.61 mmols). The reaction mixture was heated under reflux for 6 hours, and then concentrated in vacuo, which was made acidic with 1 N hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:2) to obtain the entitled compound (335 mg) as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 6 hours
  3. concentrationconcentrated in vacuo, which
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. customdried
  7. customThe solvent was evaporated out in vacuo
  8. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:2)

Sources & evidence

ORD record
ord-0e52f8ef9a8e495bb9b5ecbca4e9e062
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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