Sodium Hydroxide → 8-(2-Carboxy-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid

HRID 2268444Notes

Reaction equation

HRID 2268444 reaction equation
C([O:3][C:4]([C:6]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[CH2:14][C:13]2[C:8](=[C:9]([O:21][CH3:22])[C:10]([O:19][CH3:20])=[C:11]([O:17][CH3:18])[C:12]=2[O:15][CH3:16])[CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([C:6]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:7][C:8]2[C:13](=[C:12]([O:15][CH3:16])[C:11]([O:17][CH3:18])=[C:10]([O:19][CH3:20])[C:9]=2[O:21][CH3:22])[CH2:14]1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18348627Ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoate

Product 1

HCID 183486098-(2-Carboxy-4,5,6,7-tetramethoxyindan-2-yl)octanoic acidYield 50.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprised of an ethanol (4 ml) solution of ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoate (200 mg, 0.416 mmols) and an aqueous sodium hydroxide solution (3 M, 0.553 ml, 1.66 mmols) was heated under reflux for 12 hours. The reaction mixture was concentrated in vacuo, which was made acidic with 1 N hydrochloric acid, followed by extraction 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=1:2 to ethyl acetate only) to obtain the entitled compound (88.6 mg) as an oil.

Workup

  1. temperatureunder reflux for 12 hours
  2. concentrationThe reaction mixture was concentrated in vacuo, which
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. customThe solvent was evaporated out in vacuo
  7. customthe resulting crude product was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-bcd1824db3bf48939d93665195bb5ca3
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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