Sodium Hydroxide → 2-[4-(4-Carboxy-1-oxabutyl)phenyl]-4,5,6,7-tetramethoxy-2-indancarboxylic acid

HRID 2268462Notes

Reaction equation

HRID 2268462 reaction equation
[OH-].[Na+].C([O:5][C:6]([CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([C:35]([O:37]CC)=[O:36])[CH2:26][C:25]3[C:20](=[C:21]([O:33][CH3:34])[C:22]([O:31][CH3:32])=[C:23]([O:29][CH3:30])[C:24]=3[O:27][CH3:28])[CH2:19]2)=[CH:14][CH:13]=1)=[O:7])C>C(O)C>[C:6]([CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2([C:35]([OH:37])=[O:36])[CH2:26][C:25]3[C:20](=[C:21]([O:33][CH3:34])[C:22]([O:31][CH3:32])=[C:23]([O:29][CH3:30])[C:24]=3[O:27][CH3:28])[CH2:19]2)=[CH:16][CH:17]=1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18348634Ethyl 2-[4-(4-ethoxycarbonyl-1-oxabutyl)phenyl]-4,5,6,7-tetramethoxy-2-indancarboxylate

Product 1

HCID 183485312-[4-(4-Carboxy-1-oxabutyl)phenyl]-4,5,6,7-tetramethoxy-2-indancarboxylic acidYield 98.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous sodium hydroxide solution (3 N, 0.440 ml, 1.32 mmols) was added to an ethanol (4 ml) solution of ethyl 2-[4-(4-ethoxycarbonyl-1-oxabutyl)phenyl]-4,5,6,7-tetramethoxy-2-indancarboxylate (342 mg, 0.662 mmols), and heated under reflux for 6 hours. The reaction mixture was concentrated in vacuo, diluted with water, made acidic by adding 10% 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, and the resulting crude product was purified by recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (300 mg) as crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with water
  5. additionby adding 10% hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  8. customdried
  9. customThe solvent was evaporated out
  10. customthe resulting crude product was purified by recrystallization (from hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5dc831d02d724274a8b5f004692b15dc
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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