Sodium Hydroxide → 7-(4-Ethylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid

HRID 2228192Notes

Reaction equation

HRID 2228192 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][C:15]([C:19]([O:21]CC)=[O:20])=[CH:14][C:13]=3[CH:24]=2)=[CH:5][CH:4]=1)[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][C:15]([C:19]([OH:21])=[O:20])=[CH:14][C:13]=3[CH:24]=2)=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18472614Ethyl 7-(4-ethylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate

Product 1

HCID 184724057-(4-Ethylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acidYield 83.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 7—(4-ethylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (430 mg) in ethanol (20 ml) was added 1N sodium hydroxide (4.0 ml) at room temperature, and the mixture was stirred for 24 hours and concentrated under reduced pressure. To the residue was added 1N hydrochloric acid (15 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated to give crystals, which were collected by filtration to give 7—(4-ethylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (328 mg) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added 1N hydrochloric acid (15 ml)
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customto give crystals, which
  8. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-4a7691f8f42e414db4e0878dff67f6dc
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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