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

HRID 1387933Notes

Reaction equation

HRID 1387933 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:20][CH2:19][CH2:18][C:17]([C:21]([O:23]CC)=[O:22])=[CH:16][C:15]=3[CH:26]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:20][CH2:19][CH2:18][C:17]([C:21]([OH:23])=[O:22])=[CH:16][C:15]=3[CH:26]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18472239Ethyl 7-(4-tert-butylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate

Product 1

HCID 184722187-(4-Tert-butylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acidYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 7-(4-tert-butylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (503.8 mg) in ethanol (10 ml) was added 1N sodium hydroxide (2.0 m) at room temperature, and the mixture was stirred for 64 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. The resulting crystal was collected by filtration to give 7-(4-tert-butyl-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (396 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. filtrationThe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-61148bffcf9b42388300c8e267249010
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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