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

HRID 2268459Notes

Reaction equation

HRID 2268459 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([C:34]([O:36]CC)=[O:35])[CH2:25][C:24]3[C:19](=[C:20]([O:32][CH3:33])[C:21]([O:30][CH3:31])=[C:22]([O:28][CH3:29])[C:23]=3[O:26][CH3:27])[CH2:18]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2([C:34]([OH:36])=[O:35])[CH2:25][C:24]3[C:19](=[C:20]([O:32][CH3:33])[C:21]([O:30][CH3:31])=[C:22]([O:28][CH3:29])[C:23]=3[O:26][CH3:27])[CH2:18]2)=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18348586Ethyl 2-(4-benzyloxyphenyl)-4,5,6,7-tetramethoxy-2-indancarboxylate

Product 1

HCID 183485202-(4-Benzyloxyphenyl)-4,5,6,7-tetramethoxy-2-indancarboxylic acidYield 76.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous sodium hydroxide solution (3 N, 0.204 ml, 0.612 mmols) was added to an ethanol (4 ml) solution of ethyl 2-(4-benzyloxyphenyl)-4,5,6,7-tetramethoxy-2-indancarboxylate (150 mg, 0.305 mmols), and heated under reflux for 6 hours. The reaction mixture was concentrated in vacuo, and was made acidic by adding 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 recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (108 mg) as crystals.

Workup

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

Sources & evidence

ORD record
ord-1076f04c97f24aa09006489df8b7ee06
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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