Sodium hydride → 4-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoic acid

HRID 2268497Notes

Reaction equation

HRID 2268497 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][O:16][C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][CH:18]=3)[CH2:12][CH2:13][C:7]=2[C:6]([O:28][CH3:29])=[C:5]([O:30][CH3:31])[C:4]=1[O:32][CH3:33].[H-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:26][CH:27]=3)[CH2:12][CH2:13][C:7]=2[C:6]([O:28][CH3:29])=[C:5]([O:30][CH3:31])[C:4]=1[O:32][CH3:33]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 18348644Ethyl 4-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoate

Product 1

HCID 183486524-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoic acidYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of ethyl 4-[2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoate (1.77 g), aqueous sodium hydride (3N, 1.93 ml), and methanol (30 ml) was heated under reflux for 6 hr. The reaction mixture was concentrated in vacuo, diluted with water, made acidic with 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 THF-diisopropylether to yield the entitled compound (1.34 g) as crystals.

Workup

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

Sources & evidence

ORD record
ord-7125c719bbb442bab22b22a6989c0267
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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